. beta.-Lactam annulation using (phenylthio) nitromethane

AGM Barrett, GG Graboski, M Sabat…

文献索引：Barrett, Anthony G. M.; Graboski, Gregory G.; Sabat, Michal; Taylor, Sven J. Journal of Organic Chemistry, 1987 , vol. 52, # 21 p. 4693 - 4702

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被引用次数: 23

摘要

0. h cox 0 4 cox 10 a X= SPh 11 a X= SPh b X= OCH, Ph b X= OCH, Ph convenient and far superior. The derived nitroalkene 23 reacted smoothly with 4-phenyl-2-azetidinone (4a) 12 in the presence of base to produce the nitronate 5a. This was not isolated but was directly ozonolyzed in situ6 to produce the p-lactam phenyl thio ester 5b as a mixture of diastereoisomers (1: 1.3). In the optimum reaction (41%), potassium tert-butoxide in tert- ...