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
收藏
页码：2794 / 2797
页数：4
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