Enantioselective synthesis of 2-allyl and 2-(3-trimethylsilylpropargyl)-2-hydroxycyclohexanone using osmium-catalyzed asymmetric dihydroxylation

The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-β occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving ( R, R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1998-05, Vol.9 (9), p.1619-1626
Main Authors: Devaux, Jean-Michel, Goré, Jacques, Vatèle, Jean-Michel
Format: Article
Language:English
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Summary:The catalytic asymmetric dihydroxylation of (1-cyclohexenyl) or (1-cyclopentenyl) acetonitrile 5 and 15 with AD-mix-β occurred with good enantiofacial selectivity (87 to 94.7% ee after recrystallization) giving ( R, R)-diols in agreement with the mnemonic device. The 6-membered ring diol nitrile was easily transformed, via standard functional group manipulations, to 2-allyl and 2-(3-trimethylsilylprop-2-ynyl)-2-hydroxycyclohexanone in about 35% overall yield.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(98)00144-X