biostudies-literature00570Gietter-Burch AANCRR NIH HHSNIGMS NIH HHSNIH HHS5468-71https://www.ebi.ac.uk/biostudies/studies/S-EPMC4795467biostudies-literatureUnknown17(21)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.Organic lettersHighly Diastereoselective Michael Reactions Using ?-Nitrocarbonyl Nucleophiles.PMC4795467R01 GM102358P20 GM103541S10 RR02692S10 OD016267Gietter-Burch AAWatson DAMitrut RE57falseHighly Diastereoselective Michael Reactions Using ?-Nitrocarbonyl Nucleophiles.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.2015-01-01T00:00:00Z2015 Nov2020-10-29T13:14:52Z2019-03-27T02:11:20ZS-EPMC47954672650215710.1021/acs.orglett.5b02832