N-sulfinyl metalloenamine conjugate additions: asymmetric synthesis of piperidines

Hillary M Peltier; Jonathan A Ellman

doi:10.1021/jo051020s

N-sulfinyl metalloenamine conjugate additions: asymmetric synthesis of piperidines

J Org Chem. 2005 Sep 2;70(18):7342-5. doi: 10.1021/jo051020s.

Authors

Hillary M Peltier¹, Jonathan A Ellman

Affiliation

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

PMID: 16122257
DOI: 10.1021/jo051020s

Abstract

[reaction: see text] The first examples of conjugate additions of N-tert-butanesulfinyl metalloenamines are reported. Highly stereoselective conjugate additions (97:3 to 99:1 dr) were observed between metalloenamines derived from N-sulfinyl ketimines and alpha,beta-unsaturated ketones bearing either alkyl or aryl substituents. The conjugate addition products could rapidly be converted with high diastereoselectivity to 2,4,6-trisubstituted piperidines, which are difficult to access by other methods.