Asymmetric and Site-Selective [3+2]-Annulations for the Synthesis of High-Value Bicyclic Lactams

被引：23

作者：

Kalaitzakis, Dimitris ^{[1
]}

Sofiadis, Manolis ^{[1
]}

Triantafyllakis, Myron ^{[1
]}

Daskalakis, Konstantinos ^{[1
]}

Vassilikogiannakis, Georgios ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Iraklion 71003, Crete, Greece

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 04期

关键词：

ALPHA; BETA-UNSATURATED GAMMA-BUTYROLACTAMS; VINYLOGOUS MICHAEL ADDITION; DIARYLPROLINOL SILYL ETHERS; ONE-POT SYNTHESIS; SIMPLE FURANS; ENANTIOSELECTIVE SYNTHESIS; ORGANOCATALYSIS; SCAFFOLDS; CHEMISTRY; NUCLEOPHILES;

D O I：

10.1021/acs.orglett.8b00076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric and site-selective formal [3 + 2]-annulations of gamma-alkyl-beta,gamma-unsaturated gamma-lactams with alpha,beta-unsaturated aldehydes have been developed. These organo-catalysed transformations yield high value enantioenriched bicyclic gamma-lactams with up to four new stereocenters (some-times including a quarternary carbon). The overall transformation starts from simple and readily accessible furans and oversees a rapid, controlled, and dramatic enhancement in 3D complexity.

引用

页码：1146 / 1149

页数：4

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