Mechanism of an Organoboron-Catalyzed Domino Reaction: Kinetic and Computational Studies of Borinic Acid-Catalyzed Regioselective Chloroacylation of 2,3-Epoxy Alcohols
A mechanistic study of the borinic acid-catalyzed chloroacylation of 2,3-epoxy alcohols is presented. In this unusual mode of catalysis, the borinic acid activates the substrate toward sequential reactions with a nucleophile (epoxide ring-opening by chloride) and an electrophile (O-acylation of the...
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| Published in | Journal of organic chemistry Vol. 82; no. 2; pp. 1085 - 1095 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
20.01.2017
Amer Chemical Soc |
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| Abstract | A mechanistic study of the borinic acid-catalyzed chloroacylation of 2,3-epoxy alcohols is presented. In this unusual mode of catalysis, the borinic acid activates the substrate toward sequential reactions with a nucleophile (epoxide ring-opening by chloride) and an electrophile (O-acylation of the resulting alkoxide). Reaction progress kinetic analysis of data obtained through in situ FTIR spectroscopy is consistent with a mechanism involving turnover-limiting acylation of a chlorohydrin-derived borinic ester. This proposal is further supported by investigations of the effects of aroyl chloride substitution on reaction rate. The kinetics experiments also shed light on the effects of chloride concentration on reaction rate and indicate that the catalyst is subject to inhibition by the product of the chloroacylation reaction. Computational modeling is employed to gain insight into the effects of the organoboron catalyst on the regioselectivities of the epoxide ring-opening and acylation steps. The density functional theory calculations provide a plausible pathway for selective chlorinolysis at C-3 and benzoylation at O-1, as is observed experimentally. |
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| AbstractList | A mechanistic study of the borinic acid-catalyzed chloroacylation of 2,3-epoxy alcohols is presented. In this unusual mode of catalysis, the borinic acid activates the substrate toward sequential reactions with a nucleophile (epoxide ring-opening by chloride) and an electrophile (O-acylation of the resulting alkoxide). Reaction progress kinetic analysis of data obtained through in situ FTIR spectroscopy is consistent with a mechanism involving turnover-limiting acylation of a chlorohydrin-derived borinic ester. This proposal is further supported by investigations of the effects of aroyl chloride substitution on reaction rate. The kinetics experiments also shed light on the effects of chloride concentration on reaction rate and indicate that the catalyst is subject to inhibition by the product of the chloroacylation reaction. Computational modeling is employed to gain insight into the effects of the organoboron catalyst on the regioselectivities of the epoxide ring-opening and acylation steps. The density functional theory calculations provide a plausible pathway for selective chlorinolysis at C-3 and benzoylation at O-1, as is observed experimentally. |
| Author | Tanveer, Kashif Garrett, Graham E Taylor, Mark S |
| AuthorAffiliation | Department of Chemistry |
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| Author_xml | – sequence: 1 givenname: Graham E orcidid: 0000-0001-8558-2027 surname: Garrett fullname: Garrett, Graham E – sequence: 2 givenname: Kashif surname: Tanveer fullname: Tanveer, Kashif – sequence: 3 givenname: Mark S orcidid: 0000-0003-3424-4380 surname: Taylor fullname: Taylor, Mark S email: mtaylor@chem.utoronto.ca |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28055213$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja5029809 10.1021/jo026253n 10.1021/ja00236a051 10.1021/jacs.5b05841 10.1002/anie.201408732 10.1093/hesc/9780198558934.001.0001 10.1021/jo00376a068 10.1021/ja00538a077 10.1063/1.464913 10.1021/ja00508a002 10.1002/1521-3773(20010803)40:15<2815::AID-ANIE2815>3.0.CO;2-F 10.1021/ja110332r 10.1021/jo300532f 10.1002/anie.201200304 10.1039/c39840000387 10.1021/jo970959d 10.1039/p29850000983 10.1021/ol503091n 10.1021/ja302549c 10.1021/ol502264y 10.1021/cr00004a001 10.1021/jo049494z 10.1021/ol902322r 10.1002/poc.1790 10.1055/s-2008-1072724 10.1039/p29750000963 10.1021/jo00209a047 10.1002/anie.200462544 10.1021/cs4000848 10.2174/1385272033486792 10.1039/C5CC06177F 10.1016/j.tetlet.2003.10.001 10.1039/p29880001353 10.1021/ol034455f 10.1021/acs.accounts.5b00428 10.1021/jo00350a051 10.1021/ar500371z 10.1055/s-1997-3207 10.1021/ar00167a003 10.1021/acs.orglett.5b01541 10.1071/CH11294 10.1039/c5cc06177f |
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| Keywords | DIOLS METHODOLOGY ENTRY RECOGNITION SN2 NUCLEOPHILIC-SUBSTITUTION TRIGONAL CARBON TUNGSTEN DERIVATIVES CHLORIDE |
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| References | ref9/cit9 ref6/cit6 ref3/cit3 ref27/cit27 ref18/cit18 ref23/cit23a ref23/cit23b ref25/cit25 ref8/cit8a ref10/cit10a ref8/cit8c ref10/cit10b ref8/cit8b ref8/cit8e ref21/cit21b ref8/cit8d ref8/cit8f ref14/cit14 ref21/cit21a ref2/cit2c ref2/cit2b ref5/cit5 ref2/cit2a ref1/cit1b ref20/cit20 ref17/cit17 ref26/cit26 ref4/cit4a ref4/cit4b ref4/cit4c ref19/cit19 ref12/cit12 ref15/cit15 ref11/cit11b Kirby A. J. (ref16/cit16) 1996 Katsuki T. (ref1/cit1a) 2004 ref11/cit11a ref22/cit22 ref13/cit13 ref7/cit7b ref7/cit7a ref4/cit4d ref24/cit24 Oishi, S (WOS:000304345800022) 2012; 51 Mori, Y (WOS:000170361800005) 2001; 40 Infante, I (WOS:000182825000004) 2003; 68 HAN, CC (WOS:A1987F689800051) 1987; 109 KATSUKI, T (WOS:A1980KE71000076) 1980; 102 Ishihara, K (WOS:A1997XT05100004) 1997; 62 Dimitrijevic, E (WOS:000318589100020) 2013; 3 HANSON, RM (WOS:A1991FT26000001) 1991; 91 BENTLEY, TW (WOS:A1985AMN7100017) 1985 Wang, C (WOS:000370453900003) 2016; 49 Blackmond, DG (WOS:000360867000001) 2015; 137 Wang, C (WOS:000345470000029) 2014; 16 Becke, A. D. (INSPEC:4414853) 1993; 98 Tanveer, K (WOS:000358395500027) 2015; 17 BEHRENS, CH (WOS:A1985AYM1100051) 1985; 50 KEVILL, DN (WOS:A1975AM70000019) 1975 KEVILL, DN (WOS:A1988P261300043) 1988 Fox, JM (WOS:000224492000047) 2004; 69 Wang, C (WOS:000336078400028) 2014; 136 WILLIAMS, A (WOS:A1989CA05400003) 1989; 22 Katsuki, T. (000392569500026.20) 2004 Tomata, Y (WOS:000186693800013) 2003; 44 Frisch, M. J. (000392569500026.13) 2009 Lee, D (WOS:000304027100042) 2012; 134 Pena, PCA (WOS:000181427600002) 2003; 7 Taylor, MS (WOS:000349806300017) 2015; 48 Kirby, A. J. (000392569500026.23) 1996 KO, SY (WOS:A1986F587600068) 1986; 51 Ruff, F (WOS:000291361200007) 2011; 24 Chudzinski, MG (WOS:000297064200009) 2011; 64 Lee, D (WOS:000272038200032) 2009; 11 Blackmond, DG (WOS:000230521800007) 2005; 44 El Dine, TM (WOS:000363666000015) 2015; 51 Mello, R (WOS:000304129400021) 2012; 77 Lee, D (WOS:000288889900011) 2011; 133 ASUBIOJO, OI (WOS:A1979HB60500002) 1979; 101 Uesugi, S (WOS:000341344600016) 2014; 16 BENTLEY, TW (WOS:A1984SJ24600043) 1984 Ishihara, K (WOS:A1997XJ38400022) 1997 CARON, M (WOS:A1985AGT8600047) 1985; 50 Tanaka, Y (WOS:000256803100031) 2008 Wang, C (WOS:000345833100054) 2014; 53 Sasaki, M (WOS:000182824300049) 2003; 5 |
| References_xml | – ident: ref4/cit4a doi: 10.1021/ja5029809 – ident: ref15/cit15 doi: 10.1021/jo026253n – ident: ref23/cit23b doi: 10.1021/ja00236a051 – ident: ref26/cit26 – ident: ref10/cit10b doi: 10.1021/jacs.5b05841 – ident: ref4/cit4c doi: 10.1002/anie.201408732 – volume-title: Stereoelectronic Effects year: 1996 ident: ref16/cit16 doi: 10.1093/hesc/9780198558934.001.0001 – ident: ref2/cit2c doi: 10.1021/jo00376a068 – ident: ref1/cit1b doi: 10.1021/ja00538a077 – ident: ref27/cit27 doi: 10.1063/1.464913 – ident: ref23/cit23a doi: 10.1021/ja00508a002 – ident: ref8/cit8c doi: 10.1002/1521-3773(20010803)40:15<2815::AID-ANIE2815>3.0.CO;2-F – ident: ref11/cit11a doi: 10.1021/ja110332r – ident: ref24/cit24 doi: 10.1021/jo300532f – ident: ref8/cit8e doi: 10.1002/anie.201200304 – ident: ref21/cit21a doi: 10.1039/c39840000387 – ident: ref8/cit8b doi: 10.1021/jo970959d – ident: ref21/cit21b doi: 10.1039/p29850000983 – ident: ref4/cit4b doi: 10.1021/ol503091n – ident: ref12/cit12 doi: 10.1021/ja302549c – ident: ref5/cit5 doi: 10.1021/ol502264y – ident: ref2/cit2a doi: 10.1021/cr00004a001 – ident: ref18/cit18 doi: 10.1021/jo049494z – volume-title: Organic Reactions year: 2004 ident: ref1/cit1a – ident: ref25/cit25 doi: 10.1021/ol902322r – ident: ref19/cit19 doi: 10.1002/poc.1790 – ident: ref8/cit8d doi: 10.1055/s-2008-1072724 – ident: ref14/cit14 doi: 10.1039/p29750000963 – ident: ref3/cit3 doi: 10.1021/jo00209a047 – ident: ref10/cit10a doi: 10.1002/anie.200462544 – ident: ref9/cit9 doi: 10.1021/cs4000848 – ident: ref2/cit2b doi: 10.2174/1385272033486792 – ident: ref8/cit8f doi: 10.1039/C5CC06177F – ident: ref7/cit7b doi: 10.1016/j.tetlet.2003.10.001 – ident: ref22/cit22 doi: 10.1039/p29880001353 – ident: ref7/cit7a doi: 10.1021/ol034455f – ident: ref4/cit4d doi: 10.1021/acs.accounts.5b00428 – ident: ref17/cit17 doi: 10.1021/jo00350a051 – ident: ref11/cit11b doi: 10.1021/ar500371z – ident: ref8/cit8a doi: 10.1055/s-1997-3207 – ident: ref20/cit20 doi: 10.1021/ar00167a003 – ident: ref6/cit6 doi: 10.1021/acs.orglett.5b01541 – ident: ref13/cit13 doi: 10.1071/CH11294 – start-page: 1353 year: 1988 ident: WOS:A1988P261300043 article-title: NUCLEOPHILIC-SUBSTITUTION AT TRIGONAL CARBON .4. SUBSTITUENT EFFECTS IN THE REACTIONS OF ALIPHATIC ACYL CHLORIDES WITH METHANOL AND PHENOL IN ACETONITRILE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 – volume: 7 start-page: 555 year: 2003 ident: WOS:000181427600002 article-title: The chemistry of epoxy alcohols publication-title: CURRENT ORGANIC CHEMISTRY – volume: 24 start-page: 480 year: 2011 ident: WOS:000291361200007 article-title: Concerted SN2 mechanism for the hydrolysis of acid chlorides: comparisons of reactivities calculated by the density functional theory with experimental data publication-title: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY doi: 10.1002/poc.1790 – volume: 44 start-page: 4302 year: 2005 ident: WOS:000230521800007 article-title: Reaction progress kinetic analysis: A powerful methodology for mechanistic studies of complex catalytic reactions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200462544 – volume: 17 start-page: 3482 year: 2015 ident: WOS:000358395500027 article-title: Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b01541 – year: 2004 ident: 000392569500026.20 article-title: Asymmetric Epoxidation of Allylic Alcohols: the Katsuki Sharpless Epoxidation Reaction publication-title: Organic Reactions – volume: 48 start-page: 295 year: 2015 ident: WOS:000349806300017 article-title: Catalysis Based on Reversible Covalent Interactions of Organoboron Compounds publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar500371z – start-page: 963 year: 1975 ident: WOS:A1975AM70000019 article-title: NUCLEOPHILIC-SUBSTITUTION AT TRIGONAL CARBON .2. ETHANOLYSIS OF ALIPHATIC ACYL CHLORIDES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 – volume: 16 start-page: 5937 year: 2014 ident: WOS:000345470000029 article-title: Tungsten-, Molybdenum-, and Cerium-Promoted Regioselective and Stereospecific Halogenation of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides publication-title: ORGANIC LETTERS doi: 10.1021/ol503091n – volume: 77 start-page: 4706 year: 2012 ident: WOS:000304129400021 article-title: Epoxidation of Olefins with a Silica-Supported Peracid in Supercritical Carbon Dioxide under Flow Conditions publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo300532f – volume: 64 start-page: 1466 year: 2011 ident: WOS:000297064200009 article-title: Borinic Acids: A Neglected Class of Organoboron Compounds for Recognition of Diols in Aqueous Solution publication-title: AUSTRALIAN JOURNAL OF CHEMISTRY doi: 10.1071/CH11294 – volume: 51 start-page: 16084 year: 2015 ident: WOS:000363666000015 article-title: Borinic acid catalysed peptide synthesis publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c5cc06177f – volume: 62 start-page: 5664 year: 1997 ident: WOS:A1997XT05100004 article-title: Bis(pentafluorophenyl)borinic acid as a highly effective Oppenauer oxidation catalyst for allylic and benzylic alcohols publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 98 start-page: 5648 year: 1993 ident: INSPEC:4414853 article-title: Density-functional thermochemistry. III. The role of exact exchange publication-title: Journal of Chemical Physics – volume: 134 start-page: 8260 year: 2012 ident: WOS:000304027100042 article-title: Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja302549c – year: 2009 ident: 000392569500026.13 publication-title: Gaussian 09 – volume: 137 start-page: 10852 year: 2015 ident: WOS:000360867000001 article-title: Kinetic Profiling of Catalytic Organic Reactions as a Mechanistic Tool publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b05841 – start-page: 1239 year: 2008 ident: WOS:000256803100031 article-title: Diarylborinic acid derivatives as a catalytic iminium ion generator in the Mannich-type reaction using secondary amines, aldehydes, and ketene silyl acetals publication-title: SYNLETT doi: 10.1055/s-2008-1072724 – volume: 91 start-page: 437 year: 1991 ident: WOS:A1991FT26000001 article-title: THE SYNTHETIC METHODOLOGY OF NONRACEMIC GLYCIDOL AND RELATED 2,3-EPOXY ALCOHOLS publication-title: CHEMICAL REVIEWS – volume: 53 start-page: 13920 year: 2014 ident: WOS:000345833100054 article-title: Tungsten-Catalyzed Regio- and Enantioselective Aminolysis of trans-2,3-Epoxy Alcohols: An Entry to Virtually Enantiopure Amino Alcohols publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201408732 – volume: 22 start-page: 387 year: 1989 ident: WOS:A1989CA05400003 article-title: CONCERTED MECHANISMS OF ACYL GROUP TRANSFER-REACTIONS IN SOLUTION publication-title: ACCOUNTS OF CHEMICAL RESEARCH – start-page: 597 year: 1997 ident: WOS:A1997XJ38400022 article-title: Diarylborinic acids as efficient catalysts for selective dehydration of aldols publication-title: SYNLETT – volume: 44 start-page: 8975 year: 2003 ident: WOS:000186693800013 article-title: The first C2 selective halide substitution reaction of 2,3-epoxy alcohols by the use of (CH3O)3B-MX (X=I, Br, Cl) system publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2003.10.001 – volume: 11 start-page: 5486 year: 2009 ident: WOS:000272038200032 article-title: Boron-Catalyzed Direct Aldol Reactions of Pyruvic Acids publication-title: ORGANIC LETTERS doi: 10.1021/ol902322r – start-page: 387 year: 1984 ident: WOS:A1984SJ24600043 article-title: SN2 CHARACTER OF HYDROLYSIS OF BENZOYL CHLORIDE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 49 start-page: 193 year: 2016 ident: WOS:000370453900003 article-title: Metal-Catalyzed Directed Regio- and Enantioselective Ring-Opening of Epoxides publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/acs.accounts.5b00428 – start-page: 983 year: 1985 ident: WOS:A1985AMN7100017 article-title: COMPETING SN2 AND CARBONYL ADDITION PATHWAYS FOR SOLVOLYSES OF BENZOYL CHLORIDE IN AQUEOUS-MEDIA publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 – volume: 136 start-page: 6888 year: 2014 ident: WOS:000336078400028 article-title: Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja5029809 – volume: 51 start-page: 5395 year: 2012 ident: WOS:000304345800022 article-title: Double Molecular Recognition with Aminoorganoboron Complexes: Selective Alcoholysis of β-Dicarbonyl Derivatives publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201200304 – volume: 101 start-page: 3715 year: 1979 ident: WOS:A1979HB60500002 article-title: GAS-PHASE NUCLEOPHILIC DISPLACEMENT-REACTIONS OF NEGATIVE-IONS WITH CARBONYL-COMPOUNDS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 50 start-page: 1557 year: 1985 ident: WOS:A1985AGT8600047 article-title: TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 3 start-page: 945 year: 2013 ident: WOS:000318589100020 article-title: Organoboron Acids and Their Derivatives as Catalysts for Organic Synthesis publication-title: ACS CATALYSIS doi: 10.1021/cs4000848 – year: 1996 ident: 000392569500026.23 publication-title: Stereoelectronic Effects – volume: 40 start-page: 2815 year: 2001 ident: WOS:000170361800005 article-title: Catalytic use of a boron source for boron enolate mediated stereoselective aldol reactions in water publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 5 start-page: 1789 year: 2003 ident: WOS:000182824300049 article-title: The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates:: The first endo-mode epoxide-opening reaction through an intramolecular metal chelate publication-title: ORGANIC LETTERS doi: 10.1021/ol034455f – volume: 133 start-page: 3724 year: 2011 ident: WOS:000288889900011 article-title: Borinic Acid-Catalyzed Regioselective Acylation of Carbohydrate Derivatives publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja110332r – volume: 69 start-page: 7317 year: 2004 ident: WOS:000224492000047 article-title: Computational studies of nucleophilic substitution at carbonyl carbon: the SN2 mechanism versus the tetrahedral intermediate in organic synthesis publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo049494z – volume: 102 start-page: 5974 year: 1980 ident: WOS:A1980KE71000076 article-title: THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 16 start-page: 4408 year: 2014 ident: WOS:000341344600016 article-title: Eu(OTf)3-Catalyzed Highly Regioselective Nucleophilic Ring Opening of 2,3-Epoxy Alcohols: An Efficient Entry to 3-Substituted 1,2-Diol Derivatives publication-title: ORGANIC LETTERS doi: 10.1021/ol502264y – volume: 68 start-page: 3773 year: 2003 ident: WOS:000182825000004 article-title: A first theoretical study on the origin of the metal-mediated regioselective opening of 2,3-epoxy alcohols publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo026253n – volume: 50 start-page: 5696 year: 1985 ident: WOS:A1985AYM1100051 article-title: SELECTIVE TRANSFORMATIONS OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-3 OR CARBON-2 publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 109 start-page: 589 year: 1987 ident: WOS:A1987F689800051 article-title: INTERMEDIATES AND TRANSITION-STATES IN CHLORIDE-ION ACYL CHLORIDE DISPLACEMENT-REACTIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 51 start-page: 5413 year: 1986 ident: WOS:A1986F587600068 article-title: INSITU OPENING OF EPOXY ALCOHOLS - A CONVENIENT ALTERNATIVE TO THE ISOLATION OF UNSTABLE EPOXY ALCOHOLS publication-title: JOURNAL OF ORGANIC CHEMISTRY |
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| Snippet | A mechanistic study of the borinic acid-catalyzed chloroacylation of 2,3-epoxy alcohols is presented. In this unusual mode of catalysis, the borinic acid... |
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| SubjectTerms | acylation alcohols catalysts catalytic activity chemical structure Chemistry Chemistry, Organic chlorides Fourier transform infrared spectroscopy kinetics Lewis acids Lewis bases organic chemistry Physical Sciences regioselectivity Science & Technology |
| Title | Mechanism of an Organoboron-Catalyzed Domino Reaction: Kinetic and Computational Studies of Borinic Acid-Catalyzed Regioselective Chloroacylation of 2,3-Epoxy Alcohols |
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