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Properties and reactions of substituted 1,2-thiazetidine 1,1-dioxides: Acylation of β-sultams at C-4, reduction of 4-acyl-β-sultams, and stereochemistry of 4-(α-hydroxyalkyl)-β-sultams

✍ Scribed by Müller, Martin ;Otto, Hans-Hartwig

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
827 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Acylation of N‐silylated and 2,3‐substituted 1,2‐thiazetidine 1,1‐dioxides (β‐sultams) results in the formation of 4‐acylated β‐sultams 2 and 8. The desilylation of 2 to 3 is easily done with TBAF either on silica gel or in ethanolic solution. The acylated β‐sultams are reduced by sodium borohydride yielding α‐hydroxyalkyl β‐sultams 11 and 12, obtained as mixtures of diastereoisomers. These are separated by CC. The stereochemistry of the acylated and of the α‐hydroxylated β‐sultams is elucidated by spectroscopic methods, and compared to that of the antibiotic drug thienamycin.

📜 SIMILAR VOLUMES

Properties and Reactions of Substituted
Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: 4-Alkylidene-β-sultams
✍ Müller, Martin ;Otto, Hans-Hartwig 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 615 KB

## Abstract 4‐α‐Hydroxyalkylated β‐sultams 1/5 are transformed into 4‐alkylidene‐β‐sultams 4/7 by elimination and desilylation reactions. Another route to an exocyclic double bond in the β‐sultam system has been found to be the Peterson olefination starting from 4 silylated β‐sultams 8, 10, and 11.

Properties and Reactions of Substituted
Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: Functionalization and Reactions at C(4) of the β-Sultam
✍ Herbert Plagge; Nico Manicone; Hans-Hartwig Otto 📂 Article 📅 2004 🏛 John Wiley and Sons 🌐 German ⚖ 248 KB

## Abstract The introduction of functional groups at the 4‐position of the __β__‐sultam ring was realized by the synthesis of mono‐ and disubstituted derivatives by reactions of __N__‐silylated __β__‐sultams with electrophiles in the presence of BuLi or LDA. As electrophiles, ketones, chlorosilanes