Tetrahedron: Asymmetry

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

JM Devaux, J Goré, JM Vatèle

Index: Devaux, Jean-Michel; Gore, Jacques; Vatele, Jean-Michel Tetrahedron Asymmetry, 1998 , vol. 9, # 9 p. 1619 - 1626

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Citation Number: 8

Abstract

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 ...