High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates

Tamio Hayashi; Atsushi Okada; Toshimasa Suzuka; Motoi Kawatsura

doi:10.1021/ol0343562

High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates

Org Lett. 2003 May 15;5(10):1713-5. doi: 10.1021/ol0343562.

Authors

Tamio Hayashi¹, Atsushi Okada, Toshimasa Suzuka, Motoi Kawatsura

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. thayashi@kuchem.kyoto-u.ac.jp

PMID: 12735759
DOI: 10.1021/ol0343562

Abstract

[reaction: see text] Rhodium-catalyzed asymmetric allylic alkylation of 1-substituted 2-propenyl acetates with dimethyl malonate proceeded with high enantioselectivity in the presence of cesium carbonate as a base and a rhodium catalyst generated from Rh(dpm)(C(2)H(4))(2) (dpm = dipivaloylmethanato) and a chiral phosphino-oxazoline whose basic skeleton is axially chiral binaphthyl to give branch alkylation products in greater than 90% ee.