Stereocontrolled reduction of 2-(p-tolylsulfinyl) cycloalkanones under basic conditions: π-facial selection in cyclic systems directed by a chiral side chain

K Ogura, M Ishida, M Fujita

Index: Ogura; Ishida; Fujita Bulletin of the Chemical Society of Japan, 1989 , vol. 62, # 12 p. 3987 - 3993

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Citation Number: 9

Abstract

Reduction of a 2-(p-tolylsulfinyl) cycloalkanone with sodium borohydride in methanol– triethylamine is accompanied by rapid epimerization at C 2. Under the conditions employed here, the π-facial selectivity of the reduction is directed by the side chain chirality and, among four possible isomers of the corresponding cycloalkanol, one isomer is given with high selectivities up to 85%.