American Chemical Society
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Highly Diastereoselective Michael Reactions Using β‑Nitrocarbonyl Nucleophiles

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journal contribution
posted on 2015-11-06, 00:00 authored by Amber A. S. Gietter-Burch, Roxana E. Mitrut, Donald A. Watson
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.