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Updated: Mar 31, 2026

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Highly Diastereoselective Michael Reactions Using β-Nitrocarbonyl Nucleophiles
Amber A S Gietter-Burch1, Roxana E Mitrut1, Donald A Watson1
1Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.
Abstract:
We have discovered a highly diastereoselective Michael reaction of α-substituted, β-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.
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