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