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

Paddon-Row, Michael; Kwan, Laurence; Willis, Anthony; Sherburn, Michael

Description

(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.

CollectionsANU Research Publications
Date published: 2008
Type: Journal article
URI: http://hdl.handle.net/1885/52195
Source: Angewandte Chemie International Edition
DOI: 10.1002/anie.200802002

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