Sulfoxides, aryl substituted, optically

Ogawa, S. Furukawa, N. Regiospecific ortho lithiation of o-halophenyl p-tolyl sulfoxides and synthesis of met -substituted optically active aryl alcohols./. Org. Chem. 1991, 56, 5723-5726. 

Other phosphorous compounds, as shown in Table 8, were resolved by the same procedure. The three isomeric phosphinates 27b-d containing a methyl group attached to the aryl substituent could also be resolved, irrespective of the methyl position. From the related phosphine oxides 28a d, however, only those with R=H (28a) and R=m-CH (28c) could be well resolved no satisfactory resolution could be obtained for the other isomers of 28. The efficiency of the optical resolution of alkylaryl-substituted sulfoxides and selenoxides was found to depend similarly on the type of substitution on the aryl ring. 

The Andersen synthesis of chiral sulfoxides has also been extended to diastereomerically or enantiomerically pure arenesulfinamides, which on treatment with methyllithium give optically active methyl aryl sulfoxides (83,85). The use of menthyl sulfinates in the synthesis of sulfoxides has been exploited in the preparation of optically active sulfoxides 47 and 48, which are chiral by virtue of isotopic substitution, H- D (86), and (87), respectively. More recent... 

Since we wanted to prepare a series of chiral acetylenic sulfoxides with different substituents on the aryl moiety, we needed access to the corresponding chiral sulfinates. Optically pure (-)-menthyl-p-toluenesulfinate (6 a) is commercially available but the other sulfinates (6b and 6c) are not. They were prepared according to an efficient procedure developed by Sharpless [9] from substituted benzenesulfonyl chlorides which are commercially available (Scheme 2). The sulfinates were formed as a mixture of diastereomers by in situ reduction of the... 

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