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

页码：9128 / 9132

页数：5

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