Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones

Dirk J Spielvogel; Stephen L Buchwald

doi:10.1021/ja017545t

Nickel-BINAP catalyzed enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones

J Am Chem Soc. 2002 Apr 10;124(14):3500-1. doi: 10.1021/ja017545t.

Authors

Dirk J Spielvogel¹, Stephen L Buchwald

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

PMID: 11929227
DOI: 10.1021/ja017545t

Abstract

A Ni(0)-BINAP system is utilized for the highly enantioselective alpha-arylation of alpha-substituted gamma-butyrolactones with aryl chlorides and bromides. alpha-Quaternization is achieved in moderate to excellent yields. Furthermore, the rate accelerating effect caused by the addition of Zn(II) salts is investigated.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
Naphthalenes / chemistry*
Nickel / chemistry*
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

BINAP, 2-naphthol
Naphthalenes
Organometallic Compounds
Nickel
4-Butyrolactone

Grants and funding

GM 46059/GM/NIGMS NIH HHS/United States