ISSN:
0947-3440
Keywords:
β-Sultams
;
1,2-Thiazetidines
;
Sulfonamides
;
Sulfur heterocycles
;
C—C coupling
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 course of such reactions, a portion of the C-3-substituted β-sultam is consumed in a retro-Michael-type reaction, leading to the open-chained sulfonamides 8 and 13 as side products. In the case of reactions between 5 and silyl enol ethers of cyclic ketones 16, only such open-chained products, 17, are isolated. Reactions of 5 with substituted malonates yield the β-sultams 19 and 20. Structures and stereochemistry are elucidated by spectroscopic methods.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970632
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