Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen

Authors
Davies, HML Nagashima, T Klino, JL
Citation
Hml. Davies et al., Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen, ORG LETT, 2(6), 2000, pp. 823-826
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
6
Year of publication
2000
Pages
823 - 826
Database
ISI
SICI code
1523-7060(20000323)2:6<823:SOMACO>2.0.ZU;2-H
Abstract
Dirhodium tetrakis(S(N-dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4))- catalyzed decomposition of methyl phenyldiazoacetate in the presence of 1,1 -diarylethylenes results in intermolecular cyclopropanation with high enant ioselectivity (up to 99% ee) and moderate diastereoselectivity (up to 80% d e). The reaction was applied to the asymmetric synthesis of a cyclopropyl a nalogue of tamoxifen.