85 カルボニル基の超高選択的不斉還元反応とプロスタグランジン合成への応用

概要

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Efforts made on the basis of a concept, the differentiation via a single chiral species, have realized an exceptionally stereoselective transformation. A complex hydride reagent formed from LiAlH_4, (R)- or (S)-2,2'-dihydroxy-1,1'-binaphthyl, and ethanol (1:1:1 ratio) exhibits extremely high enantioface-differentiating ability in the reduction of prochiral aromatic carbonyl compounds. Thus the reaction with 1-phenyl-1-butanone and 1-phenyl-1-pentanone in THF at -100 to -78℃ gives rise to the corresponding carbinols in virtually 100% optical yield. Further the reduction with this hydride reagent provides a powerful tool in generation of the 15S configuration in prostaglandin intermediates.
1979-09-20