Abstract
Gilman reagent (lithium dimethylcuprate) adds stereoselectively (98%) to ( E)-and ( Z)-steroidal 22-en-24-ones to yield 22 R-methylated product regardless of the geometry of the enones. The same reagent adds with complete reversal selectivity to the ( E)-and ( Z)-enones in the presence of TMSCl to yield 22 R-and 22 S-methyl-24-ketones, respectively.
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