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Rhodium‐Catalyzed Cyclopropanation of Alkenes with Dimethyl Diazomalonate
Author(s) -
GonzálezBobes Francisco,
Fenster Michaël D. B.,
Kiau Susanne,
Kolla Laxma,
Kolotuchin Sergei,
Soumeillant Maxime
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800027
Subject(s) - cyclopropanation , chemistry , alkene , rhodium , reagent , catalysis , malonate , limiting , organic chemistry , carbenoid , medicinal chemistry , mechanical engineering , engineering
The outstanding ability of dirhodium α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropanoate [Rh 2 (esp) 2 ; esp=α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate‐derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.