Enantioselective Ring Opening of Aza and Oxabicyclic Alkenes with Dimethylzinc

M Lautens; S Hiebert; JL Renaud

doi:10.1021/ol006052a

Enantioselective Ring Opening of Aza and Oxabicyclic Alkenes with Dimethylzinc

Org Lett. 2000 Jun 29;2(13):1971-1973. doi: 10.1021/ol006052a.

Authors

M Lautens¹, S Hiebert, JL Renaud

Affiliation

¹ Department of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6.

PMID: 10891204
DOI: 10.1021/ol006052a

Abstract

A system for efficient, asymmetric alkylative ring opening of azabenzonorbornadienes and [2.2.1] and [3.2.1] oxabicyclic alkenes was developed. The use of Pd(CH(3)CN)(2)Cl(2) and chiral phosphinooxazoline ligands gives the dihydronaphthalenes, cyclohexenols, and cycloheptenols in excellent yields and enantiomeric excesses.