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Properties and reactions of substituted 1,2-thiazetidine 1,1-dioxides: Synthesis of 1,2-thiazetidine-2,3-diacetic acid derivatives and their rearrangement to 1,2-thiazinan-3-ones

✍ Scribed by Schwenkkraus, Peter ;Otto, Hans-Hartwig

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
771 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

β‐Sultam‐3‐acetic acid ester 3 prepared from rac‐S‐benzyl‐β‐homocysteine is alkylated with bromoacetates yielding diacetates 9 which are transformed into the phenylthio esters 11. The thiazinanone derivatives 12 are obtained from 11 by rearrangement with lithium bis(trimethylsilyl)amide in excellent yields, and the syntheses of the derivatives 13, 14, and 15 are described. The stereochemistry of all products is elucidated by spectroscopic methods, and a reaction pathway is proposed. It is supported by the synthesis of the isomeric β‐sultam‐2,3‐diacetate 20, which does not rearrange to a thiazinanone derivative. Some side reactions are described. magnified image

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