Synthesis of Aminocyclobutanes through Ring Expansion of N-Vinyl-β-Lactams

被引：30
作者：
Cheung, Lawrence L. W. [1 ]
Yudin, Andrei K. [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 06期
基金：
加拿大自然科学与工程研究理事会;
关键词：
STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; CYCLOADDITIONS; PATHWAYS;
D O I：
10.1021/ol900118d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing delta-lactams can be accessed from N-vinyl-beta-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane delta-lactams in a diastereoselective manner.
引用
收藏
页码：1281 / 1284
页数：4
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