Tetrahedron

Highly stereoselective 1, 4-asymmetric reactions of 2-(arylsulfinyl) benzaldehydes and 2-(arylsulfinyl) phenyl ketones

S Nakamura, M Oda, H Yasuda, T Toru

Index: Nakamura, Shuichi; Oda, Masahiro; Yasuda, Hiroki; Toru, Takeshi Tetrahedron, 2001 , vol. 57, # 40 p. 8469 - 8480

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Citation Number: 25

Abstract

The Grignard reaction of 2-(arylsulfinyl) benzaldehydes and the DIBAL reduction of 2- (arylsulfinyl) phenyl ketones were examined. The sterically bulky (2, 4, 6-trimethylphenyl)- and (2, 4, 6-triisopropylphenyl) sulfinyl groups were shown to effect high 1, 4-remote asymmetric induction. The optically active 1-phenyl-1-p-tolylmethanol could be efficiently prepared by desulfinylation of the Grignard reaction product obtained from chiral [(2, 4, 6- ...