Au-Catalyzed Piperidine Synthesis via Tandem Acyloxy Migration/Intramolecular [3 + 2] Cycloaddition of Enynyl Esters
An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules.
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Published in | Organic letters Vol. 13; no. 24; pp. 6448 - 6451 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
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American Chemical Society
16.12.2011
Amer Chemical Soc |
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Abstract | An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules. |
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AbstractList | An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules. |
Author | Zhao, Changgui Jing, Peng Yang, Juan Fang, Bowen Zheng, Huaiji She, Xuegong Huo, Xing |
AuthorAffiliation | Lanzhou University Chinese Academy of Sciences |
AuthorAffiliation_xml | – name: Chinese Academy of Sciences – name: Lanzhou University |
Author_xml | – sequence: 1 givenname: Huaiji surname: Zheng fullname: Zheng, Huaiji – sequence: 2 givenname: Xing surname: Huo fullname: Huo, Xing – sequence: 3 givenname: Changgui surname: Zhao fullname: Zhao, Changgui – sequence: 4 givenname: Peng surname: Jing fullname: Jing, Peng – sequence: 5 givenname: Juan surname: Yang fullname: Yang, Juan – sequence: 6 givenname: Bowen surname: Fang fullname: Fang, Bowen – sequence: 7 givenname: Xuegong surname: She fullname: She, Xuegong |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/22085340$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1021/ja003168t 10.1002/adsc.200900614 10.1021/ja050845g 10.1039/b615629k 10.1002/chem.200601522 10.1016/j.jorganchem.2004.03.001 10.1021/om0607200 10.1021/cr0684319 10.1021/cr000436x 10.1002/chem.200801387 10.2174/138527206778018203 10.1002/anie.200907078 10.1021/ja074824t 10.1021/ja0717717 10.1351/pac200476030453 10.1021/ja057327q 10.1002/ejoc.201100179 10.1021/cr020009e 10.1002/anie.201006633 10.1021/ol052610f 10.1021/ol052229v 10.1002/anie.200502999 10.1002/anie.200701589 10.1002/anie.200604773 10.1021/ja005570d 10.1002/chem.200400089 10.1021/ja1095045 10.1002/anie.200604335 10.1002/adsc.200600368 10.1039/b209175p 10.1002/chem.200600174 10.1002/anie.200462568 10.1002/chem.201000009 10.1021/ja804690u 10.1002/adsc.201000201 10.1021/ja910346m 10.1021/ja01646a005 10.1021/cr980054f 10.1039/b308768a |
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Keywords | ACTIVATION GOLD CATALYSIS EFFICIENT SYNTHESIS PLATINUM CYCLOISOMERIZATION BOND REARRANGEMENTS CYCLIZATION 1,N-ENYNES |
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References | Hashmi A. S. K. (ref8/cit8o) 2000; 122 Fürstner A. (ref3/cit3b) 2005; 127 Ma S. (ref8/cit8f) 2006; 45 Hashmi A. S. K. (ref6/cit6) 2009; 351 Cai S. (ref2/cit2b) 2011; 50 Hashmi A. S. K. (ref11/cit11) 2010; 49 Codell G. A. (ref1/cit1b) 2000; 54 Kim N. (ref4/cit4i) 2005; 7 Yang C.-Y. (ref4/cit4b) 2010; 352 Marion N. (ref9/cit9a) 2007; 46 Partyka D. V. (ref4/cit4g) 2007; 26 Hashmi A. S. K. (ref5/cit5a) 2011 Echavarren A. M. (ref8/cit8i) 2004; 33 Zhang L. (ref5/cit5b) 2006; 128 Añrbe L. (ref8/cit8j) 2004; 10 Hashmi A. S. K. (ref9/cit9d) 2007; 107 Zhang G. (ref4/cit4d) 2008; 130 Adè A. (ref4/cit4j) 2004; 689 Méndez M. (ref8/cit8k) 2003; 16 Michelet V. (ref8/cit8b) 2008; 47 Echavarren A. M. (ref8/cit8l) 2004; 76 Fürstner A. (ref9/cit9c) 2007; 46 Melhado A. D. (ref4/cit4a) 2011; 133 Jiménez-Núñez E. (ref8/cit8a) 2008; 108 Lloyd-Jones G. (ref8/cit8m) 2003; 1 Zhang L. (ref8/cit8e) 2006; 348 Marco-Contelles J. (ref9/cit9b) 2007; 13 Aubert C. (ref8/cit8n) 2002; 102 Marion N. (ref10/cit10) 2009; 15 Hashmi A. S. K. (ref4/cit4k) 2008; 37 Melhado A. D. (ref4/cit4e) 2007; 129 Kusama H. (ref4/cit4h) 2006; 8 Lutton J. M. (ref3/cit3a) 1954; 76 Zhang Z. (ref8/cit8d) 2006; 10 Bruneau C. (ref8/cit8g) 2005; 44 Huang X. (ref4/cit4f) 2007; 129 Diver S. T. (ref8/cit8h) 2004; 104 Li C.-W. (ref4/cit4c) 2010; 16 Nieto-Oberhuber C. (ref8/cit8c) 2006; 12 Trost B. M. (ref1/cit1a) 2000; 122 Zheng H. (ref2/cit2a) 2010; 132 MENDEZ M (WOS:000297717800031.31) 2003; 16 Marion, N (WOS:000264674300025) 2009; 15 Trost, BM (WOS:000165696900037) 2000; 122 Furstner, A (WOS:000246538200006) 2007; 46 Hashmi, ASK (WOS:000165600300051) 2000; 122 CAI S (WOS:000297717800031.5) 2011; 50 Hashmi, ASK (WOS:000289361100008) 2011; 2011 CODELL GA (WOS:000297717800031.6) 2000; 54 Huang, XG (WOS:000246535300027) 2007; 129 Anorbe, L (WOS:000224600600001) 2004; 10 Partyka, DV (WOS:000243086800027) 2007; 26 Kim, N (WOS:000233259000045) 2005; 7 Aubert, C (WOS:000174456500008) 2002; 102 Yang, CY (WOS:000280657900007) 2010; 352 LUTTON, JM (WOS:A1954UB50600005) 1954; 76 Ma, SM (WOS:000234441900004) 2006; 45 Hashmi, ASK (WOS:000247926600008) 2007; 107 Diver, ST (WOS:000220153100006) 2004; 104 Zhang, LM (WOS:000242471700003) 2006; 348 Kusama, H (WOS:000234657900029) 2006; 8 Hashmi, ASK (WOS:000259408300002) 2008; 37 Echavarren, AM (WOS:000223760400004) 2004; 33 Ade, A (WOS:000221212200010) 2004; 689 Melhado, AD (WOS:000250327000026) 2007; 129 Nieto-Oberhuber, C (WOS:000239750900003) 2006; 12 Zhang, LM (WOS:000235224700023) 2006; 128 Echavarren, AM (WOS:000221367800002) 2004; 76 Marco-Contelles, J (WOS:000244220400001) 2007; 13 Marion, N (WOS:000245904700002) 2007; 46 Zhang, GZ (WOS:000259295400024) 2008; 130 Lloyd-Jones, GC (WOS:000181557300001) 2003; 1 Bruneau, C (WOS:000228709200006) 2005; 44 Li, CW (WOS:000278349700034) 2010; 16 Furstner, A (WOS:000229751100006) 2005; 127 Melhado, AD (WOS:000288410100052) 2011; 133 Hashmi, ASK (WOS:000280464200003) 2010; 49 Zhang, Z (WOS:000238932600007) 2006; 10 Hashmi, ASK (WOS:000272392000018) 2009; 351 Michelet, V (WOS:000256364400006) 2008; 47 Zheng, HJ (WOS:000275085000028) 2010; 132 Jimenez-Nunez, E (WOS:000259077600021) 2008; 108 |
References_xml | – volume: 122 start-page: 12007 year: 2000 ident: ref1/cit1a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja003168t – volume: 351 start-page: 2855 year: 2009 ident: ref6/cit6 publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200900614 – volume: 127 start-page: 8244 year: 2005 ident: ref3/cit3b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja050845g – volume: 37 start-page: 1766 year: 2008 ident: ref4/cit4k publication-title: Chem. Soc. Rev. doi: 10.1039/b615629k – volume: 13 start-page: 1350 year: 2007 ident: ref9/cit9b publication-title: Chem.—Eur. J. doi: 10.1002/chem.200601522 – volume: 689 start-page: 1788 year: 2004 ident: ref4/cit4j publication-title: J. Organomet. Chem. doi: 10.1016/j.jorganchem.2004.03.001 – volume: 26 start-page: 183 year: 2007 ident: ref4/cit4g publication-title: Organometallics doi: 10.1021/om0607200 – volume: 108 start-page: 3326 year: 2008 ident: ref8/cit8a publication-title: Chem. Rev. doi: 10.1021/cr0684319 – volume: 107 start-page: 3180 year: 2007 ident: ref9/cit9d publication-title: Chem. Rev. doi: 10.1021/cr000436x – volume: 15 start-page: 3243 year: 2009 ident: ref10/cit10 publication-title: Chem.—Eur. J. doi: 10.1002/chem.200801387 – volume: 10 start-page: 1457 year: 2006 ident: ref8/cit8d publication-title: Curr. Org. Chem. doi: 10.2174/138527206778018203 – volume: 49 start-page: 5232 year: 2010 ident: ref11/cit11 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200907078 – volume: 129 start-page: 12638 year: 2007 ident: ref4/cit4e publication-title: J. Am. Chem. Soc. doi: 10.1021/ja074824t – volume: 129 start-page: 6398 year: 2007 ident: ref4/cit4f publication-title: J. Am. Chem. Soc. doi: 10.1021/ja0717717 – volume: 76 start-page: 453 year: 2004 ident: ref8/cit8l publication-title: Pure Appl. Chem. doi: 10.1351/pac200476030453 – volume: 128 start-page: 1442 year: 2006 ident: ref5/cit5b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja057327q – start-page: 2256 year: 2011 ident: ref5/cit5a publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201100179 – volume: 104 start-page: 1317 year: 2004 ident: ref8/cit8h publication-title: Chem. Rev. doi: 10.1021/cr020009e – volume: 50 start-page: 1 year: 2011 ident: ref2/cit2b publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201006633 – volume: 8 start-page: 289 year: 2006 ident: ref4/cit4h publication-title: Org. Lett. doi: 10.1021/ol052610f – volume: 7 start-page: 5289 year: 2005 ident: ref4/cit4i publication-title: Org. Lett. doi: 10.1021/ol052229v – volume: 45 start-page: 200 year: 2006 ident: ref8/cit8f publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200502999 – volume: 47 start-page: 4268 year: 2008 ident: ref8/cit8b publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200701589 – volume: 46 start-page: 2750 year: 2007 ident: ref9/cit9a publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200604773 – volume: 122 start-page: 11553 year: 2000 ident: ref8/cit8o publication-title: J. Am. Chem. Soc. doi: 10.1021/ja005570d – volume: 10 start-page: 4938 year: 2004 ident: ref8/cit8j publication-title: Chem.—Eur. J. doi: 10.1002/chem.200400089 – volume: 133 start-page: 3517 year: 2011 ident: ref4/cit4a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja1095045 – volume: 46 start-page: 3410 year: 2007 ident: ref9/cit9c publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200604335 – volume: 348 start-page: 2271 year: 2006 ident: ref8/cit8e publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200600368 – volume: 1 start-page: 215 year: 2003 ident: ref8/cit8m publication-title: Org. Biomol. Chem. doi: 10.1039/b209175p – volume: 16 start-page: 397 year: 2003 ident: ref8/cit8k publication-title: Chemtracts – volume: 12 start-page: 5916 year: 2006 ident: ref8/cit8c publication-title: Chem.—Eur. J. doi: 10.1002/chem.200600174 – volume: 44 start-page: 2328 year: 2005 ident: ref8/cit8g publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200462568 – volume: 16 start-page: 5803 year: 2010 ident: ref4/cit4c publication-title: Chem.—Eur. J. doi: 10.1002/chem.201000009 – volume: 130 start-page: 12598 year: 2008 ident: ref4/cit4d publication-title: J. Am. Chem. Soc. doi: 10.1021/ja804690u – volume: 352 start-page: 1605 year: 2010 ident: ref4/cit4b publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.201000201 – volume: 54 volume-title: The Alkaloids: Chemistry and Biology year: 2000 ident: ref1/cit1b – volume: 132 start-page: 1788 year: 2010 ident: ref2/cit2a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja910346m – volume: 76 start-page: 4271 year: 1954 ident: ref3/cit3a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01646a005 – volume: 102 start-page: 813 year: 2002 ident: ref8/cit8n publication-title: Chem. Rev. doi: 10.1021/cr980054f – volume: 33 start-page: 431 year: 2004 ident: ref8/cit8i publication-title: Chem. Soc. Rev. doi: 10.1039/b308768a – volume: 49 start-page: 5232 year: 2010 ident: WOS:000280464200003 article-title: Homogeneous Gold Catalysis Beyond Assumptions and Proposals-Characterized Intermediates publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200907078 – volume: 2011 start-page: 2256 year: 2011 ident: WOS:000289361100008 article-title: Gold Catalysis: Products and Intermediates Obtained from N-Propargylcarboxamides Bearing Additional Substituents on Nitrogen publication-title: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY doi: 10.1002/ejoc.201100179 – volume: 33 start-page: 431 year: 2004 ident: WOS:000223760400004 article-title: Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b308768a – volume: 10 start-page: 1457 year: 2006 ident: WOS:000238932600007 article-title: Transition metal-catalyzed intramolecular enyne cyclization reaction publication-title: CURRENT ORGANIC CHEMISTRY – volume: 47 start-page: 4268 year: 2008 ident: WOS:000256364400006 article-title: Cycloisomerization of 1,n-enynes: Challenging metal-catalyzed rearrangements and mechanistic insights publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 10 start-page: 4938 year: 2004 ident: WOS:000224600600001 article-title: Reorganization of enynes catalyzed by platinum salts publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200400089 – volume: 348 start-page: 2271 year: 2006 ident: WOS:000242471700003 article-title: Gold and platinum catalysis of enyne cycloisomerization publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200600368 – volume: 44 start-page: 2328 year: 2005 ident: WOS:000228709200006 article-title: Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200462568 – volume: 122 start-page: 11553 year: 2000 ident: WOS:000165600300051 article-title: Highly selective gold-catalyzed arene synthesis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja005570d – volume: 8 start-page: 289 year: 2006 ident: WOS:000234657900029 article-title: Pt(II)- or Au(III)-catalyzed [3+2] cycloaddition of metal-containing azomethine ylides: Highly efficient synthesis of the mitosene skeleton publication-title: ORGANIC LETTERS doi: 10.1021/ol052610f – volume: 133 start-page: 3517 year: 2011 ident: WOS:000288410100052 article-title: Gold(I)-Catalyzed Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition and Mannich Reactions of Azlactones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja1095045 – volume: 108 start-page: 3326 year: 2008 ident: WOS:000259077600021 article-title: Gold-catalyzed cycloisomerizations of enynes: A mechanistic perspective publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0684319 – volume: 15 start-page: 3243 year: 2009 ident: WOS:000264674300025 article-title: Gold- and Platinum-Catalyzed Cycloisomerization of Enynyl Esters versus Allenenyl Esters: An Experimental and Theoretical Study publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200801387 – volume: 76 start-page: 4271 year: 1954 ident: WOS:A1954UB50600005 article-title: THE REACTION BETWEEN PLATINUM CHLORIDES AND CARBON MONOXIDE - THE PREPARATION AND CONFIGURATION OF DICHLORODICARBONYLPLATINUM(II) publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 50 start-page: 1 year: 2011 ident: WOS:000297717800031.5 publication-title: ANGEW CHEM INT EDIT – volume: 122 start-page: 12007 year: 2000 ident: WOS:000165696900037 article-title: A ruthenium-catalyzed pyrrolidine and piperidine synthesis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 104 start-page: 1317 year: 2004 ident: WOS:000220153100006 article-title: Enyne metathesis (enyne bond reorganization) publication-title: CHEMICAL REVIEWS – volume: 76 start-page: 453 year: 2004 ident: WOS:000221367800002 article-title: Metal cyclopropyl carbenes in the reactions of alkynes with alkenes and furans publication-title: PURE AND APPLIED CHEMISTRY – volume: 129 start-page: 12638 year: 2007 ident: WOS:000250327000026 article-title: Au(I)-catalyzed enantioselective 1,3-dipolar cycloadditions of Munchnones with electron-deficient Alkenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja074824t – volume: 352 start-page: 1605 year: 2010 ident: WOS:000280657900007 article-title: Gold-Catalyzed Synthesis of Bicyclo[3.2.0]heptenes via a Formal [3+2]/[2+2]-Annulation of Allylsilane with 4-Methoxybut-2-yn-1-ols publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201000201 – volume: 1 start-page: 215 year: 2003 ident: WOS:000181557300001 article-title: Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY – volume: 130 start-page: 12598 year: 2008 ident: WOS:000259295400024 article-title: Au-containing all-carbon 1,3-dipoles: Generation and [3+2] cycloaddition reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja804690u – volume: 46 start-page: 3410 year: 2007 ident: WOS:000246538200006 article-title: Catalytic carbophilic activation: Catalysis by platinum and gold pi acids publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200604335 – volume: 689 start-page: 1788 year: 2004 ident: WOS:000221212200010 article-title: Organometallic gold(III) and gold(I) complexes as catalysts for the 1,3-dipolar cycloaddition to nitrones: synthesis of novel gold-nitrone derivatives publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY doi: 10.1016/j.jorganchem.2004.03.001 – volume: 7 start-page: 5289 year: 2005 ident: WOS:000233259000045 article-title: Gold-catalyzed cycloisomerization of o-alkynylbenzaldehydes with a pendant unsaturated bond: [3+2] cycloaddition of gold-bound 1,3-dipolar species with dipolarophiles publication-title: ORGANIC LETTERS doi: 10.1021/ol052229v – volume: 102 start-page: 813 year: 2002 ident: WOS:000174456500008 article-title: The behavior of 1,n-enynes in the presence of transition metals publication-title: CHEMICAL REVIEWS doi: 10.1021/cr980054f – volume: 46 start-page: 2750 year: 2007 ident: WOS:000245904700002 article-title: Propargylic esters in gold catalysis: Access to diversity publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200604773 – volume: 45 start-page: 200 year: 2006 ident: WOS:000234441900004 article-title: Gold-catalyzed cyclization of enynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200502999 – volume: 128 start-page: 1442 year: 2006 ident: WOS:000235224700023 article-title: Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja057327q – volume: 26 start-page: 183 year: 2007 ident: WOS:000243086800027 article-title: Carbon-gold bond formation through [3+2] cycloaddition reactions of gold(I) azides and terminal alkynes publication-title: ORGANOMETALLICS doi: 10.1021/om0607200 – volume: 54 year: 2000 ident: WOS:000297717800031.6 publication-title: ALKALOIDS CHEM BIOL – volume: 107 start-page: 3180 year: 2007 ident: WOS:000247926600008 article-title: Gold-catalyzed organic reactions publication-title: CHEMICAL REVIEWS doi: 10.1021/cr000436x – volume: 127 start-page: 8244 year: 2005 ident: WOS:000229751100006 article-title: Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja050845g – volume: 37 start-page: 1766 year: 2008 ident: WOS:000259408300002 article-title: Gold catalysis in total synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b615629k – volume: 129 start-page: 6398 year: 2007 ident: WOS:000246535300027 article-title: Two-step formal [3+2] cycloaddition of enones/enals and allenyl MOM ether: Gold-catalyzed highly diastereoselective synthesis of cyclopentanone enol ether containing an all-carbon quaternary center publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0717717 – volume: 16 start-page: 397 year: 2003 ident: WOS:000297717800031.31 publication-title: CHEMTRACTS ORG CHEM – volume: 351 start-page: 2855 year: 2009 ident: WOS:000272392000018 article-title: Gold Catalysis: Anellated Heterocycles and Dependency of the Reaction Pathway on the Tether Length publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200900614 – volume: 13 start-page: 1350 year: 2007 ident: WOS:000244220400001 article-title: Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200601522 – volume: 12 start-page: 5916 year: 2006 ident: WOS:000239750900003 article-title: The mechanistic puzzle of transition-metal-catalyzed skeletal rearrangements of enynes publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200600174 – volume: 16 start-page: 5803 year: 2010 ident: WOS:000278349700034 article-title: Construction of 2,3-Dihydrofuran Cores through the [3+2] Cycloaddition of Gold alpha-Carbonylcarbenoids with Alkenes publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201000009 – volume: 132 start-page: 1788 year: 2010 ident: WOS:000275085000028 article-title: Pt-Catalyzed Tandem 1,2-Acyloxy Migration/Intramolecular [3+2] Cycloaddition of Enynyl Esters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja910346m |
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Snippet | An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy... |
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SubjectTerms | Alkynes - chemistry Catalysis Chemistry Chemistry, Organic Combinatorial Chemistry Techniques Cyclization Esters Gold - chemistry Molecular Structure Physical Sciences Piperidines - chemical synthesis Piperidines - chemistry Science & Technology Stereoisomerism |
Title | Au-Catalyzed Piperidine Synthesis via Tandem Acyloxy Migration/Intramolecular [3 + 2] Cycloaddition of Enynyl Esters |
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