Tetrahedron Letters

Stereoselective synthesis of highly enantioenriched 3-methyl-2-cyclohexen-1-ones possessing an asymmetric quaternary carbon as C-4 or C-6: a sugar template …

H Kubo, I Kozawa, K Takao, K Tadano

Index: Kubo, Hiroto; Kozawa, Ikuko; Takao, Ken-ichi; Tadano, Kin-ichi Tetrahedron Letters, 2008 , vol. 49, # 7 p. 1203 - 1207

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Citation Number: 7

Abstract

The 1, 4-addition of the enolate generated from α-methylated acetoacetate incorporated at C- 4 of methyl 6-deoxy-2, 3-di-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside to methyl vinyl ketone, followed by aldol condensation of the resulting 1, 4-addition product under two base- mediated conditions, provided 4-O-functionalized d-glucose derivatives with high diastereoselectivity. These products install a 3-methyl-2-cyclohexen-1-one-4-(or-6-) ...