Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru-salencomplex: Solubility dependent enantioface selection

Authors
Uchida, T Irie, R Katsuki, T
Citation
T. Uchida et al., Highly cis- and enantioface-selective cyclpropanation using (R,R)-Ru-salencomplex: Solubility dependent enantioface selection, SYNLETT, (11), 1999, pp. 1793-1795
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
11
Year of publication
1999
Pages
1793 - 1795
Database
ISI
SICI code
0936-5214(199911):11<1793:HCAECU>2.0.ZU;2-5
Abstract
The reaction of styrene and t-butyl alpha-diazoacetate in the presence of ( R,R)-(ON+)(salen)ruthenium(II) complex 1 under the irradiation of incandesc ent light in THF gave the corresponding (1S,2R)-cyclopropanecarboxylate wit h high stereoselectivity of 99% ee (cis : trans = 96 : 4), while the same r eaction in hexane gave the enantiomeric (1R,2S)-cyclopropanecarboxylate pre ferentially (83% ee, cis : trans = 68 : 32).