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Asymmetric synthesis of α-hydroxy acids via β-Lactams

✍ Scribed by V. Srirajan; A.R.A.S. Deshmukh; V.G. Puranik; B.M. Bhawal

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
356 KB
Volume
7
Category
Article
ISSN
0957-4166

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✦ Synopsis

A diastereoselective synthesis of [5-Lactams 5a-e and 6a-e has been achieved, via a Staudinger reaction using imines derived from (1S)-(+)-camphor-10-sulfonamide, in good yields. The major diastereomers 6a-e were isolated in pure form by crystallization. The absolute configuration of the [5-1actam 6b was established as 3R and 4S by X-ray analysis. The major diastereomers 6b and 6c were converted into enantiomerically pure a-hydroxy ester derivatives 7-9.

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