Rh(II)-Catalyzed Cyclopropanation of Furans and Its Application to the Total Synthesis of Natural Product Derivatives

被引：42
|
作者：
Lehner, Verena [1 ,2 ]
Davies, Huw M. L. [2 ]
Reiser, Oliver [1 ]
机构：
[1] Univ Regensburg, Inst Organ Chem, Univ Str 31, D-93053 Regensburg, Germany
[2] Emory Univ, Dept Chem, 1515 Dickey Dr, Atlanta, GA 30322 USA
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 18期
基金：
美国国家科学基金会;
关键词：
ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; STABILIZED VINYLCARBENOIDS; CATALYZED DECOMPOSITION; RHODIUM CARBENOIDS; TURNOVER NUMBERS; RH(II) CATALYST; PYRROLES; DIRHODIUM(II); CONVERSION;
D O I：
10.1021/acs.orglett.7b02009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rh(II)-catalyzed enantioselective cyclopropanations of furans, providing access to synthetically useful building blocks, are reported. After screening of 10 Rh(II) catalysts, Rh-2(S-TCPTTL)(4) was identified as a highly efficient and selective catalyst (up to 98% ee, TON 88000, and TOF 24/s) for the cydopropanation of furans. These cyclopropanes were successfully applied to the enantioselective synthesis of novel paraconic acid derivatives.
引用
收藏
页码：4722 / 4725
页数：4
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