A One-Pot C-H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

被引：23
|
作者：
Lloyd, Matthew G. [1 ]
Taylor, Richard J. K. [1 ]
Unsworth, William P. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 10期
关键词：
DIRECT IMINE ACYLATION;
D O I：
10.1021/ol501092m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.
引用
收藏
页码：2772 / 2775
页数：4
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