Chiral Relay Effect: 4-Substituted 1,3-Benzoxazol-2-(3H)-ones as Achiral Templates for Enantioselective Diels−Alder Reactions
- 14 December 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (1) , 39-42
- https://doi.org/10.1021/ol016966c
Abstract
A new strategy to control the enantioselectivity of Lewis acid catalyzed reactions has been investigated. The use of N-acryloyl-1,3-benzoxazol-2-(3H)-ones substituted at position 4 leads to the formation of diastereomeric complexes as a result of the presence of a chiral axis. The stereochemical outcome of the reaction is controlled by the chiral catalyst and by the chiral axis, leading to high enantioselectivity improvements and, in one case, to an inversion of enantioselectivity.Keywords
This publication has 2 references indexed in Scilit:
- Chiral Bis(oxazoline) Copper(II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene ReactionsAccounts of Chemical Research, 2000
- C2-Symmetric chiral bis(oxazoline)–metal complexes in catalytic asymmetric synthesisTetrahedron: Asymmetry, 1998