Asymmetric titanium-catalysed Michael addition of O-benzylhydroxylamine to αβ-unsaturated carbonyl compounds: synthesis of β-amino acid precursors
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 23,p. 2823-2826
- https://doi.org/10.1039/p19960002823
Abstract
A new titanium-catalysed Michael type addition of O-benzylhydroxylamine to αβ-unsaturated N-acylated 1,3-oxazolidinones giving β-amino acid precursors has been developed. The reaction is catalysed by TiX2–TADDOLate and TiCl2–BINOLate complexes and good conversions with enantiomeric excesses up to 42% were obtained with the application of 10 mol% of the catalyst. In order to determine the absolute stereochemistry of the enriched enantiomer one of the products, 3-(3-benzyloxyaminobutanoyl)-1,3-oxazolidin-2-one, was converted into methyl 3-benzoylaminobutanoate. Based on the absolute stereochemistry of the Michael type addition product the mechanism for the addition step is discussed, as well as the structure of the active intermediate.This publication has 20 references indexed in Scilit:
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