Synlett 2016; 27(01): 21-24
DOI: 10.1055/s-0035-1560530
letter
© Georg Thieme Verlag Stuttgart · New York

Bifunctional Iminophosphorane Catalyzed Enantioselective Ketimine Phospha-Mannich Reaction

Gerard P. Robertson
The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK   Email: darren.dixon@chem.ox.ac.uk
,
Alistair J. M. Farley
The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK   Email: darren.dixon@chem.ox.ac.uk
,
Darren J. Dixon*
The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK   Email: darren.dixon@chem.ox.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 06 October 2015

Accepted after revision: 24 October 2015

Publication Date:
11 November 2015 (online)


Dedicated to Professor Steven V. Ley on the occasion of his 70th birthday

Abstract

The enantioselective phospha-Mannich reaction of diethyl phosphite to unactivated N-DPP-protected ketimines catalyzed by a bifunctional iminophosphorane (BIMP) superbase organocatalyst is described. The reaction is applicable to ketimines bearing electron-rich and electron-poor aryl substituents and occurs with excellent yields and moderate enantioselectivities under mild reaction conditions.

Supporting Information