Tetrahedron

Highly enantioselective addition of primary alkyl Grignard reagents to carbocyclic and heterocyclic arylketones in the presence of magnesium TADDOLate preparative …

B Weber, D Seebach

Index: Weber, Beat; Seebach, Dieter Tetrahedron, 1994 , vol. 50, # 20 p. 6117 - 6128

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Citation Number: 107

Abstract

In the presence of equimolar amounts of the Mg alkoxide from α, α, α′, α′-tetraphenyl-2, 2- dimethyl-1, 3-dioxolan-4, 5-dimethanol (a TADDOL) primary Grignard reagents (Et, Pr, Bu, Oct, 3-butenyl) add to carbo-and heteroaromatic methyl ketones in THF at− 100° C to give tertiary alcohols of enantiomeric excesses reaching values above 98%. The scope and limitation of the method are investigated. The reaction, which occurs in a vigorously stirred ...