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cis- and Enantio-selective Cyclopropanation with Chiral (ON+)Ru–Salen Complex as a Catalyst

✍ Scribed by Tatsuya Uchida; Ryo Irie; Tsutomu Katsuki

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
146 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐCyclopropanation of styrene with a-diazoacetate in the presence of (R,R)-(salen)ruthenium complex 4 in THF which dissolves the complex exhibits remarkable cis-and enantio-selectivity [cis:trans97:3, .97% ee (1S,2R)], while the same reaction in hexane which does not dissolve it shows good but opposite sense of enantioselectivity [283% ee (1R,2S)] together with moderate cis-selectivity (cis:trans68:32). In homogeneous and heterogeneous conditions, (salen)ruthenium complexes are considered to have different ligandconformation which, in turn, causes the opposite sense of enantioface selectivity in the cyclopropanation.

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