Cyclopropylamines from N,N-Dialkylcarboxamides and Grignard Reagents in the Presence of Titanium Tetraisopropoxide or Methyltitanium Triisopropoxide
Thirty‐three different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides 9–17 were treated with unsubstituted as well as with 2‐alkyl‐, 2,2‐dialkyl‐, and 3‐alkenyl‐substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methy...
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| Published in | Chemistry : a European journal Vol. 16; no. 46; pp. 13862 - 13875 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
10.12.2010
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
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| Abstract | Thirty‐three different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides 9–17 were treated with unsubstituted as well as with 2‐alkyl‐, 2,2‐dialkyl‐, and 3‐alkenyl‐substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20–25 in 20–98 % yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98 %) of the cyclopropylamines 20–28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane‐protected ketones and halogen‐substituted and chiral as well as achiral alkyloxyalkyl‐substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl‐ and a variety of alkyl‐substituted ethylmagnesium bromides in addition to numerous heteroatom‐containing (e.g., halogen‐, trityloxy‐, tetrahydropyranyloxy‐substituted) Grignard reagents (62 examples altogether). The transformation of N,N‐diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,N‐dicyclopropyl‐N‐alkylamines 55 can be brought about in up to 82 % yield (6 examples). An asymmetric variant of the titanium‐mediated cyclopropanation of N,N‐dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84 %. Evaluation of several silyl‐based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 mol %) of the titanium reagent, as long as 2‐aryl‐ or 2‐ethenyl‐substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)‐Cotinine as well as the insecticides Dinotefuran and Imidacloprid.
Ti is it: Cyclopropylamines have been obtained in low to excellent yield through the reaction of different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides with Grignard reagents in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide (see scheme). |
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| AbstractList | Thirty‐three different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides 9–17 were treated with unsubstituted as well as with 2‐alkyl‐, 2,2‐dialkyl‐, and 3‐alkenyl‐substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20–25 in 20–98 % yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98 %) of the cyclopropylamines 20–28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane‐protected ketones and halogen‐substituted and chiral as well as achiral alkyloxyalkyl‐substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl‐ and a variety of alkyl‐substituted ethylmagnesium bromides in addition to numerous heteroatom‐containing (e.g., halogen‐, trityloxy‐, tetrahydropyranyloxy‐substituted) Grignard reagents (62 examples altogether). The transformation of N,N‐diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,N‐dicyclopropyl‐N‐alkylamines 55 can be brought about in up to 82 % yield (6 examples). An asymmetric variant of the titanium‐mediated cyclopropanation of N,N‐dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84 %. Evaluation of several silyl‐based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 mol %) of the titanium reagent, as long as 2‐aryl‐ or 2‐ethenyl‐substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)‐Cotinine as well as the insecticides Dinotefuran and Imidacloprid.
Ti is it: Cyclopropylamines have been obtained in low to excellent yield through the reaction of different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides with Grignard reagents in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide (see scheme). Thirty-three different N,N-dialkyl- and N-alkyl-N-phosphorylalkyl-substituted carboxamides 9-17 were treated with unsubstituted as well as with 2-alkyl-, 2,2-dialkyl-, and 3-alkenyl-substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20-25 in 20-98% yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98%) of the cyclopropylamines 20-28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane-protected ketones and halogen-substituted and chiral as well as achiral alkyloxyalkyl-substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl- and a variety of alkyl-substituted ethylmagnesium bromides in addition to numerous heteroatom-containing (e.g., halogen-, trityloxy-, tetrahydropyranyloxy-substituted) Grignard reagents (62 examples altogether). The transformation of N,N-diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,N-dicyclopropyl-N-alkylamines 55 can be brought about in up to 82% yield (6 examples). An asymmetric variant of the titanium-mediated cyclopropanation of N,N-dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84%. Evaluation of several silyl-based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 mol%) of the titanium reagent, as long as 2-aryl- or 2-ethenyl-substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)-Cotinine as well as the insecticides Dinotefuran and Imidacloprid. Thirty-three different N,N-dialkyl- and N-alkyl-N-phosphorylalkyl-substituted carboxamides 9-17 were treated with unsubstituted as well as with 2-alkyl-, 2,2-dialkyl-, and 3-alkenyl-substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20-25 in 20-98% yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98%) of the cyclopropylamines 20-28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane-protected ketones and halogen-substituted and chiral as well as achiral alkyloxyalkyl-substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl- and a variety of alkyl-substituted ethylmagnesium bromides in addition to numerous heteroatom-containing (e.g., halogen-, trityloxy-, tetrahydropyranyloxy-substituted) Grignard reagents (62 examples altogether). The transformation of N,N-diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,N-dicyclopropyl-N-alkylamines 55 can be brought about in up to 82% yield (6 examples). An asymmetric variant of the titanium-mediated cyclopropanation of N,N-dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84%. Evaluation of several silyl-based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 mol%) of the titanium reagent, as long as 2-aryl- or 2-ethenyl-substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)-Cotinine as well as the insecticides Dinotefuran and Imidacloprid. Abstract Thirty‐three different N , N ‐dialkyl‐ and N ‐alkyl‐ N ‐phosphorylalkyl‐substituted carboxamides 9 – 17 were treated with unsubstituted as well as with 2‐alkyl‐, 2,2‐dialkyl‐, and 3‐alkenyl‐substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20 – 25 in 20–98 % yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98 %) of the cyclopropylamines 20 – 28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane‐protected ketones and halogen‐substituted and chiral as well as achiral alkyloxyalkyl‐substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl‐ and a variety of alkyl‐substituted ethylmagnesium bromides in addition to numerous heteroatom‐containing (e.g., halogen‐, trityloxy‐, tetrahydropyranyloxy‐substituted) Grignard reagents (62 examples altogether). The transformation of N , N ‐diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N , N ‐dicyclopropyl‐ N ‐alkylamines 55 can be brought about in up to 82 % yield (6 examples). An asymmetric variant of the titanium‐mediated cyclopropanation of N , N ‐dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses ( ee ) of up to 84 %. Evaluation of several silyl‐based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 mol %) of the titanium reagent, as long as 2‐aryl‐ or 2‐ethenyl‐substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite ( S )‐Cotinine as well as the insecticides Dinotefuran and Imidacloprid. Thirty-three different N,N-dialkyl- and N-alkyl-N-phosphorylalkyl-substituted carboxamides 9-17 were treated with unsubstituted as well as with 2-alkyl-, 2,2-dialkyl-, and 3-alkenyl-substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20-25 in 20-98% yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98%) of the cyclopropylamines 20-28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane-protected ketones and halogen-substituted and chiral as well as achiral alkyloxyalkyl-substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl- and a variety of alkyl-substituted ethylmagnesium bromides in addition to numerous heteroatom-containing (e.g., halogen-, trityloxy-, tetrahydropyranyloxy-substituted) Grignard reagents (62 examples altogether). The transformation of N,N-diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,N-dicyclopropyl-N-alkylamines 55 can be brought about in up to 82% yield (6 examples). An asymmetric variant of the titanium-mediated cyclopropanation of N,N-dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84%. Evaluation of several silyl-based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25mol%) of the titanium reagent, as long as 2-aryl- or 2-ethenyl-substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)-Cotinine as well as the insecticides Dinotefuran and Imidacloprid. Thirty-three different N,N-dialkyl- and N-alkyl-N-phosphorylalkyl-substituted carboxamides 9-17 were treated with unsubstituted as well as with 2-alkyl-, 2,2-dialkyl-, and 3-alkenyl-substituted ethylmagnesium bromides 6 in the presence of stoichiometric amounts of titanium tetraisopropoxide or methyltitanium triisopropoxide to furnish substituted cyclopropylamines 20-25 in 20-98% yield, depending on the substituents with no (1:1) to excellent (>25:1) diastereoselectivities. Generally higher yields (up to 98%) of the cyclopropylamines 20-28 without loss of the diastereoselectivity were obtained with methyltitanium triisopropoxide as the titanium mediator. Under these conditions, even dioxolane-protected ketones and halogen-substituted and chiral as well as achiral alkyloxyalkyl-substituted carboxamides could be converted to the correspondingly substituted cyclopropylamines with unsubstituted as well as phenyl-and a variety of alkyl-substituted ethylmagnesium bromides in addition to numerous heteroatom-containing (e.g., halogen-, trityloxy-, tetrahydropyranyloxy-substituted) Grignard reagents (62 examples altogether). The transformation of N,N-diformylalkylamines 54 with ethylmagnesium bromide in the presence of methyltitanium triisopropoxide to N,Ndicyclopropyl-N-alkylamines 55 can be brought about in up to 82% yield (6 examples). An asymmetric variant of the titanium-mediated cyclopropanation of N,N-dialkylcarboxamides has been developed by applying chiral titanium mediators generated from stoichiometric amounts of titanium tetraisopropoxide and chiral diamino or diol ligands, respectively. The most efficient chiral mediators turned out to be titanium bistaddolates that provided the corresponding cyclopropylamines with enantiomeric excesses (ee) of up to 84%. Evaluation of several silyl-based additives revealed that the reaction can also efficiently be carried out with substoichiometric amounts (down to 25 mol%) of the titanium reagent, as long as 2-aryl- or 2-ethenyl-substituted ethylmagnesium halides are used and a concomitant slight decrease in yields is accepted. The newly developed methodology was successfully applied for the preparation of analogues with cyclopropylamine moieties of known drugs and natural products such as the nicotine metabolite (S)-Cotinine as well as the insecticides Dinotefuran and Imidacloprid. |
| Author | Stecker, Björn Schill (née Brackmann), Farina Winsel, Harald Gazizova, Vesta Chaplinski, Vladimir Boese, Roland de Meijere, Armin Kordes, Markus Savchenko, Andrei I. |
| Author_xml | – sequence: 1 givenname: Armin surname: de Meijere fullname: de Meijere, Armin email: Armin.deMeijere@chemie.uni-goettingen.de organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 2 givenname: Vladimir surname: Chaplinski fullname: Chaplinski, Vladimir organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 3 givenname: Harald surname: Winsel fullname: Winsel, Harald organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 4 givenname: Markus surname: Kordes fullname: Kordes, Markus organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 5 givenname: Björn surname: Stecker fullname: Stecker, Björn organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 6 givenname: Vesta surname: Gazizova fullname: Gazizova, Vesta organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 7 givenname: Andrei I. surname: Savchenko fullname: Savchenko, Andrei I. organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 – sequence: 8 givenname: Roland surname: Boese fullname: Boese, Roland organization: Institut für Anorganische Chemie, Universität Essen, Universitätsstrasse 3-5, 45117 Essen (Germany), Fax: (+49) 201-183-2535 – sequence: 9 givenname: Farina surname: Schill (née Brackmann) fullname: Schill (née Brackmann), Farina organization: Institut für Organische und Biomolekulare Chemie der Georg-August-Universität, Tammannstrasse 2, 37077 Göttingen (Germany), Fax: (+49) 551-399475 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20945442$$D View this record in MEDLINE/PubMed |
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| ContentType | Journal Article |
| Copyright | Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| ISSN | 0947-6539 |
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| Issue | 46 |
| Keywords | enantioselectivity ORGANIC-SYNTHESIS FUNCTIONALIZED CHLOROENAMINES CONVENIENT SYNTHESES titanium BUILDING-BLOCKS EASY ACCESS amines AMINOCYCLOPROPANE SYNTHESIS MEDIATED CYCLOPROPANATION organometallics small ring systems ETHYLMAGNESIUM BROMIDE N-CYCLOPROPYLATION CARBOXYLIC-ACIDS |
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| Notes | istex:D9A0B791613B4E4A8E74C213C545589DE8A687F1 Cyclopropyl Building Blocks for Organic Synthesis, Part 156; Part 155: A. Lygin, M. Limbach, A. Janssen, V. S. Korotkov, C. Funke, A. de Meijere, Eur. J. Org. Chem. 2010, 3665-3671. Gottlieb-Daimler- und Karl-Benz-Stiftung Land Niedersachsen ark:/67375/WNG-3394NMRQ-3 Fonds der Chemischen Industrie Otto-Vahlbruch-Stiftung ArticleID:CHEM201001550 BayerCropScience AG Karl-Ziegler-Stiftung 3665–3671. Crystal‐structure analyses. 2010 Eur. J. Org. Chem. Cyclopropyl Building Blocks for Organic Synthesis, Part 156; Part 155: A. Lygin, M. Limbach, A. Janssen, V. S. Korotkov, C. Funke, A. de Meijere ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 20945442 |
| PQID | 1766599004 |
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| PublicationCentury | 2000 |
| PublicationDate | December 10, 2010 |
| PublicationDateYYYYMMDD | 2010-12-10 |
| PublicationDate_xml | – month: 12 year: 2010 text: December 10, 2010 day: 10 |
| PublicationDecade | 2010 |
| PublicationPlace | Weinheim |
| PublicationPlace_xml | – name: Weinheim – name: WEINHEIM – name: Germany |
| PublicationSubtitle | A European Journal |
| PublicationTitle | Chemistry : a European journal |
| PublicationTitleAbbrev | CHEM-EUR J |
| PublicationTitleAlternate | Chemistry - A European Journal |
| PublicationYear | 2010 |
| Publisher | WILEY-VCH Verlag WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Publisher_xml | – name: WILEY-VCH Verlag – name: WILEY‐VCH Verlag – name: Wiley – name: Wiley Subscription Services, Inc |
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| Snippet | Thirty‐three different N,N‐dialkyl‐ and N‐alkyl‐N‐phosphorylalkyl‐substituted carboxamides 9–17 were treated with unsubstituted as well as with 2‐alkyl‐,... Thirty-three different N,N-dialkyl- and N-alkyl-N-phosphorylalkyl-substituted carboxamides 9-17 were treated with unsubstituted as well as with 2-alkyl-,... Abstract Thirty‐three different N , N ‐dialkyl‐ and N ‐alkyl‐ N ‐phosphorylalkyl‐substituted carboxamides 9 – 17 were treated with unsubstituted as well as... |
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| SubjectTerms | Alkylation amines Amines - chemistry Asymmetry Bromides Chemistry Chemistry, Multidisciplinary Cyclopropanes - chemistry Diols enantioselectivity Indicators and Reagents - chemistry Ketones Ligands Metabolites Molecular Structure Organometallic Compounds - chemistry organometallics Physical Sciences Science & Technology small ring systems Stereoisomerism Titanium Titanium - chemistry Transformations |
| Title | Cyclopropylamines from N,N-Dialkylcarboxamides and Grignard Reagents in the Presence of Titanium Tetraisopropoxide or Methyltitanium Triisopropoxide |
| URI | https://api.istex.fr/ark:/67375/WNG-3394NMRQ-3/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fchem.201001550 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000285398700032 https://www.ncbi.nlm.nih.gov/pubmed/20945442 https://www.proquest.com/docview/1766599004 https://search.proquest.com/docview/1777993552 https://search.proquest.com/docview/816386361 |
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