Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex

Vincent S Chan; Ian C Stewart; Robert G Bergman; F Dean Toste

doi:10.1021/ja058100y

Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex

J Am Chem Soc. 2006 Mar 8;128(9):2786-7. doi: 10.1021/ja058100y.

Authors

Vincent S Chan¹, Ian C Stewart, Robert G Bergman, F Dean Toste

Affiliation

¹ Department of Chemistry, University of California, Berkeley, CA 94720, USA.

PMID: 16506742
DOI: 10.1021/ja058100y

Abstract

Ruthenium phosphido complexes have been shown to be excellent nucleophiles, reacting via two-electron processes with a variety of electrophiles. A catalytic alkylation reaction was developed using an achiral ruthenium complex, which was then elaborated into a catalytic enantioselective synthesis of P-stereogenic phosphines. These useful and synthetically challenging phosphines can now be accessed in a single step from simple secondary phosphines and alkyl halides. Optimization and scope of the enantioselective alkylation are discussed.