Highly Diastereoselective Michael Reactions Using ?-Nitrocarbonyl Nucleophiles.

ABSTRACT: We have discovered a highly diastereoselective Michael reaction of ?-substituted, ?-nitrocarbonyl compounds to deliver highly functionalized stereodiads containing fully substituted nitrogen-bearing centers. Good to excellent yields and diastereoselectivities are observed. This transformation is tolerant of various types of carbonyl groups on the nucleophilic partner, as well as a range of unsaturated electrophiles. Mechanistic investigations are consistent with internal hydrogen bonding in the nitroalkane tautomer as the major factor in the control of diastereoselectivity in these transformations.

SUBMITTER: Gietter-Burch AA 

PROVIDER: S-EPMC4795467 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature