One-pot synthesis of γ-lactams from ketoaziridines

被引：3
|
作者：
Martelli, Lorena S. R. [1 ]
da Silva, Otavio A. M. [1 ]
Zukerman-Schpector, Julio [2 ]
Correa, Arlene G. [1 ]
机构：
[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil
[2] Univ Fed Sao Carlos, Dept Chem, BR-13565905 Sao Carlos, SP, Brazil
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 46期
基金：
巴西圣保罗研究基金会;
关键词：
RING EXPANSION; ASYMMETRIC AZIRIDINATION; N-H; EPOXIDATION; AGENT; (+/-)-CLAUSENAMIDE; CYCLIZATION; CHEMISTRY;
D O I：
10.1039/d3ob01568h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The remarkable biological activities of gamma-lactams have stimulated the search for efficient synthetic methods to achieve these scaffolds. In this work, we have developed a simple one-pot diastereoselective synthesis of new gamma-lactams from ketoaziridines with moderate to good yields via the Horner-Wadsworth-Emmons reaction, followed by an intramolecular ester-aziridine cyclization and its opening in situ. Preliminary efforts towards an enantioselective version of this method are also reported. New gamma-lactams were obtained in a one-pot procedure from ketoaziridines in moderate to good overall yields.
引用
收藏
页码：9128 / 9132
页数：5
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