Halodiazophosphonates, a New Class of Diazo Compounds for the Diastereoselective Intermolecular Rh(II) Catalyzed Cyclopropanation

被引：17

作者：

Schnaars, Christian ^{[1
]}

Hansen, Tore ^{[1
]}

机构：

[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 11期

关键词：

H INSERTION REACTIONS; ENANTIOSELECTIVE SYNTHESIS; DONOR/ACCEPTOR CARBENOIDS; ASYMMETRIC-SYNTHESIS; RHODIUM CARBENOIDS; CYCLOPROPYLPHOSPHONATES; ALKENES; FUNCTIONALIZATION; SELECTIVITY; ACTIVATION;

D O I：

10.1021/ol3010276

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Halodiazomethyl)phosphonates 2A-C have been generated by a one-pot procedure via a clean, efficient, and rapid deprotonation/electrophilic halogenation sequence from diethyl diazomethylphosphonate 1 (EDP). Subsequent Intermolecular Rh(II)-catalyzed cyclopropanation afforded the corresponding halocyclopropylphosphonates 3-10 in moderate to high yields and high diastereomeric ratios. Catalyst loadings down to 0.1 mol % as well as clean and selective product formation were achieved.

引用

页码：2794 / 2797

页数：4

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