Asymmetric Mukaiyama−Michael Addition of Acyclic Enones Catalyzed by allo-Threonine-Derived B-Aryloxazaborolidinones
- 1 June 2001
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (13) , 2101-2103
- https://doi.org/10.1021/ol016062r
Abstract
[reaction: see text] O-(2-Naphthoyl)-N-tosyl-L-allo-threonine-derived B-phenyloxazaborolidinone catalyzes the asymmetric Mukaiyama-Michael addition of simple acyclic enones to give adducts of 54-85% ee. 2,6-Diisopropylphenol as an additive is demonstrated to effectively retard the undesirable Si(+)-catalyzed racemic pathway.Keywords
This publication has 7 references indexed in Scilit:
- A short-step synthesis of trans-whisky lactone by an asymmetric Michael reactionTetrahedron: Asymmetry, 1998
- A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoatesTetrahedron, 1997
- Enantioselective mukaiyama-michael reactions of 2-carbomethoxy cyclopentenone catalyzed by chiral bis(Oxazoline)-Cu(II) complexesTetrahedron Letters, 1996
- Homogeneous Catalysis. Mechanisms of the Catalytic Mukaiyama Aldol and Sakurai Allylation ReactionsJournal of the American Chemical Society, 1995
- Metal versus silyl triflate catalysis in the Mukaiyama aldol addition reactionTetrahedron Letters, 1994
- Darstellung von arylhalogenboranenJournal of Organometallic Chemistry, 1986
- Asymmetric synthesis of β-substituted δ-ketoesters via michael-additions of samp/ramp-hydrazones to α,β-unsaturated esters, virtually complete 1.6-asymmetric inductionTetrahedron Letters, 1983