Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH·⋯O hydrogen bonding

Michael N. Paddon-Row; Laurence C.H. Kwan; Anthony C. Willis; Michael S. Sherburn

doi:10.1002/anie.200802002

Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH·⋯O hydrogen bonding

Michael N. Paddon-Row, Laurence C.H. Kwan, Anthony C. Willis, Michael S. Sherburn

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond.

Original language	English
Pages (from-to)	7013-7017
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	37
DOIs	https://doi.org/10.1002/anie.200802002
Publication status	Published - 1 Sept 2008

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abstract = "(Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond.",

keywords = "Asymmetric catalysis, Density functional calculations, Lewis acids, Lewis bases, Transition states",

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AU - Kwan, Laurence C.H.

AU - Willis, Anthony C.

AU - Sherburn, Michael S.

PY - 2008/9/1

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N2 - (Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond.

AB - (Chemical Equation Presented) All cis-tems go! The first detailed computational investigations into the title reaction validate Corey's two pre-transition-state models and reveal a third Lewis acid coordination mode (see picture), which operates for esters having s-cis C=C-C=O groups. The new pre-transition-state model explains the unexpected enantioselectivity witnessed for several Diels-Alder reactions and does not involve a C-H⋯O hydrogen bond.

KW - Asymmetric catalysis

KW - Density functional calculations

KW - Lewis acids

KW - Lewis bases

KW - Transition states

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ER -

Enantioselective oxazaborolidinium-catalyzed Diels-Alder reactions without CH·⋯O hydrogen bonding

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