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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...
Reactions of various 1-sulfinyl-2-naphthaldehydes with Grignard reagents were examined. The naphthaldehyde having the 2,4,6-triisopropylphenylsulfinyl group gave the product with high stereoselectivity, possibly derived from the predominant rotamer around the C-S axis. The reaction of the chiral sulfinylnaphthaldehyde with PhMgBr and subsequent elimination of the sulfinyl group gave the enantiomerically...
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