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Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.

ABSTRACT: Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity.

SUBMITTER: Trost BM

PROVIDER: S-EPMC2679032 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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Direct asymmetric Michael addition to nitroalkenes: vinylogous nucleophilicity under dinuclear zinc catalysis.

Trost Barry M BM Hitce Julien J

Journal of the American Chemical Society 20090401 13

Under dinuclear catalysis, the direct conjugate addition of 2(5H)-furanone to nitroalkenes involves the gamma-position of the nucleophile. The synthetically versatile Michael adducts are prepared in good yields, with high levels of diastereo- and enantioselectivity. A model is presented to rationalize the observed stereoselectivity. ...[more]

PMID: 19281239

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