The first highly enantioenriched, configurationally stable α-thioallyllithium compound ( 9 ) was generated by deprotonation of the S -cyclohex-2-enyl thiocarbamate 8 . The methylation of 9 in both the α- and γ-positions proceeds antarafacially with a high degree of chirality transmission, as was elucidated by X-ray analysis of thiocarbamates 10 and 11 . The optically active S -allyl thiocarbamate 8 was prepared by enantiospecific [3,3]sigmatropic rearrangement of the corresponding O -allyl thiocarbamate 7 .
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Marr et al. (1999) studied this question.
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