2-Picolyl thioesters; a useful synthon for the preparation of 1-β-alkyl carbapenem intermediates

In this study, a highly stereoselective preparation of (3S,4S)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxy-ethyl]-azetidin-2-one ( 2 ) is reported. It involves a Lewis acid mediated condensation of (3S,4R)-4-acetoxy-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one ( 3 ) with...

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Bibliographic Details
Published in:Canadian journal of chemistry 1988-06, Vol.66 (6), p.1537-1539
Main Authors: Martel, Alain, Daris, Jean-Paul, Bachand, Carol, Corbeil, Jacques, Menard, Marcel
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:In this study, a highly stereoselective preparation of (3S,4S)-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxy-ethyl]-azetidin-2-one ( 2 ) is reported. It involves a Lewis acid mediated condensation of (3S,4R)-4-acetoxy-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one ( 3 ) with simple O-silylenol ethers of thiopropionates. From all the examples reported in this paper the 2-picolyl thiopropionate or similar arrangements were found to be essential for this stereoselection. Finally, a mechanism involving chelation control seems to be operative.
ISSN:0008-4042
1480-3291
DOI:10.1139/v88-248