Highly Stereoselective Reactions of γ-Sulfinyl Carbanions with Achiral Imines

Abstract

Lithium 2-p-tolylsulfinylbenzyl carbanions react with different N-substituted imines affording 1,2-diaryl ethyl (and propyl) amines with a high stereoselectivity control at both benzyllic (only dependent of the sulfur configuration) and iminic carbons. The anti:syn ratio, ranging between > 96: < 4 and < 2: > 98, dependent on the electronic density at nitrogen.

keywords:

• 1,4- and 1,5-Asymmetric induction;
• asymmetric benzylation;
• remote stereocontrol with sulfoxides

Acknowledgments

We thank the Spanish Government for financial support (Grant BQU2003-04012). J. A. thanks the Spanish Government for a predoctoral fellowship.