Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines

Daniel J Weix; Yili Shi; Jonathan A Ellman

doi:10.1021/ja044003d

Diastereoselective and enantioselective Rh(I)-catalyzed additions of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl aldimines

J Am Chem Soc. 2005 Feb 2;127(4):1092-3. doi: 10.1021/ja044003d.

Authors

Daniel J Weix¹, Yili Shi, Jonathan A Ellman

Affiliation

¹ Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.

PMID: 15669835
DOI: 10.1021/ja044003d

Abstract

Two new Rh(I)-catalyzed methods for the synthesis of chiral alpha-branched amines via addition of arylboronic acids to N-tert-butanesulfinyl and N-diphenylphosphinoyl imines have been developed. The syntheses are more functional group tolerant than alternative methods utilizing Grignard or organolithium reagents, and the imine activating groups used are easily removed. These methods are both high-yielding (70-97% yield) and very selective (>93:7 dr and 88-94% ee). Significantly, the N-tert-butanesulfinyl imine method works for aliphatic imines with enolizable protons. In addition, a one-pot procedure for the synthesis of N-tert-butanesulfinyl protected alpha-branched amines from aldehydes has been developed.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Amines / chemical synthesis*
Boronic Acids / chemistry*
Catalysis
Imines / chemistry*
Phosphinic Acids / chemistry
Rhodium / chemistry*
Stereoisomerism
Sulfinic Acids / chemistry*

Substances

Aldehydes
Amines
Boronic Acids
Imines
Phosphinic Acids
Sulfinic Acids
Rhodium
benzeneboronic acid