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Diastereo- and enantio-selective synthesis of trans-3-phenyl- and trans-3-styryl-2-azetidinones via zinc ester enolates and imines

✍ Scribed by Henk Kleijn; Hendrik L. van Maanen; Johann T. B. H. Jastrzebski; Gerard van Koten

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
201 KB
Volume
111
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Zinc enolates of phenyl‐ and trans‐styryl‐acetic acid methyl ester react with excellent diastereoselectivety and good enantioselectivety (e.e. 64 to 91.5%) with imines in high yields to trans‐2‐azetidinones. The corresponding lithium enolates reacted with much lower selectivity and yields.

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✍ Fred H van der Steen; Johann T.B.H Jastrzebski; Gerard van Koten πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 262 KB

A new one-pot synthesis of 3-amino-g-lactams that is based on the condensation of simple imines with zinc enolates of disilyl protected glycine esters is mported Isolated yields are high and a rranr-selectivity is observed. ## with imines. With N-(benzylidene)-trimethylsilylamine the ring-closure