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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

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Highly Diastereoselective Michael Reactions Using β-Nitrocarbonyl Nucleophiles.

Gietter-Burch Amber A S AA Mitrut Roxana E RE Watson Donald A DA

Organic letters 20151026 21

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 ...[more]

PMID: 26502157

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