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Enantioselective Oxazaborolidinium‐Catalyzed Diels–Alder Reactions without CH⋅⋅⋅⋅O Hydrogen Bonding
Author(s) -
PaddonRow Michael N.,
Kwan Laurence C. H.,
Willis Anthony C.,
Sherburn Michael S.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802002
Subject(s) - enantioselective synthesis , catalysis , chemistry , hydrogen bond , diels–alder reaction , lewis acids and bases , hydrogen , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , polymer chemistry , molecule
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 CCCO groups. The new pre‐transition‐state model explains the unexpected enantioselectivity witnessed for several Diels–Alder reactions and does not involve a CH⋅⋅⋅O hydrogen bond.