Ring transformation of 1,2-thiazetidine 1,1-dioxides with Lewis acids: formation of trans-1,2,3-oxathiazolidine 2-oxides and cis-Aziridines
✍ Scribed by Tadashi Kataoka; Tetsuo Iwama
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 221 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
📜 SIMILAR VOLUMES
## 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
## 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)a
## Abstract At 0° in MeCN, 2,2‐disubstituted 3‐amino‐2__H__‐azirines 1 and 4,4‐disubstituted 1,2‐thiazetidin‐3‐one 1,1‐dioxides 7 react smoothly to give 1,2,5‐thiadiazepin‐6‐one 1,1‐dioxides of type 8 (__Scheme 2__). The reaction mechanism of this regiospecific ring enlargement to seven‐membered he