Complementary Stereochemical Outcomes in Proline-Based Self-Regenerations of Stereocenters

Abstract

Stereoselective alkylations of proline-based amino amides are described, where high levels of either a <i>cis</i> or <i>trans</i> configuration can be attained simply by the choice of the aminal group. Isobutryaldehyde-derived aminals provide the <i>cis</i> configuration, while 1-naphthaldehyde-derived aminals engender the complementary <i>trans</i> configuration