No abstract

1991 stereochemistry stereochemistry (general, optical resolution) O 0030 -067Highly Enantioselective Addition of (S)-Lithiomethyl 1-Naphthyl Sulfoxide to Ketones.-The optically active sulfoxide (I) reacts consecutively with lithium diethylamide and the ketones (II) to form mainly the (S)-configurated carbinols (III), together with minor amounts of the diastereomers (IV). The stereoselectivity of the reaction is low when dialkyl ketones, e. g. (IIa), are employed as the starting materials. In the series of the alkyl phenyl ketones (IIb) -(IIe), the diastereoselectivity decreases with the length and the sterical requirements of the alkyl group. Desulfination of (IIIb) and (IIIc) produces the (S)-configurated tertiary alcohols (V). -(SAKURABA, H.; USHIKI, S.; Tetrahedron Lett. 31 (1990) 37, 5349-5352; Dep. Ind. Chem., Fac. Eng., Kanto Gakuin Univ., Yokohama, Kanagawa 236, Japan; EN)