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Substituted 1,2-Thiazetidine 1,1-Dioxides. Synthesis and Properties of N-Alkylated and N-Acylated Derivatives of 1,2-Thiazetidine-3-acetic Acid 1,1-Dioxide

✍ Scribed by Till Röhrich; Bassam Abu Thaher; Hans-Hartwig Otto

Publisher: Springer Vienna
Year: 2004
Tongue: English
Weight: 447 KB
Volume: 135
Category: Article
ISSN: 0026-9247
DOI: 10.1007/s00706-003-0105-2

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Substituted 1,2-Thiazetidine 1,1-Dioxide

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Properties and Reactions of Substituted

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Substituted 1,2-Thiazetidine 1,1-Dioxide

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Substituted 1,2-Thiazetidine 1,1-Dioxide

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Properties and Reactions of Substituted

Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: 3-Acetoxy-1,2-thiazetidine 1,1-Dioxide, Synthesis and Reactions with C-Nucleophiles

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## Abstract __N__‐Silylated 3‐acetoxy‐1,2‐thiazetidine 1,1‐dioxide (5) is prepared from L‐cystine. Reactions of 5 with silyl enol ethers yield C‐3‐substituted β‐sultams 6, 12 and 15. Desilylation of 6 affords 7, which undergoes photochemical cyclization to give the bicyclic β‐sultam 10. In the cour

Properties and Reactions of Substituted

Properties and Reactions of Substituted 1,2-Thiazetidine 1,1-Dioxides: Chiral Mono- and Bicyclic 1,2-Thiazetidine 1,1-Dioxides from α-Amino Acids

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## Abstract New chiral mono‐ and bicyclic __β__‐sultams, valuable building blocks for drug synthesis, have been prepared from L‐Ala, L‐Val, L‐Leu, L‐Ile, L‐Phe, L‐Cys, L‐Ser, L‐Thr, and D‐penicillamine by transformation of the COOH group into a methylsulfonyl chloride function, followed by cyclizat