Enantioselective functionalization of prochiral diols via chiral spiroketals: preparation of optically pure 2-substituted 1, 3-propanediol derivatives and asymmetric …

T Harada, T Hayashiya, I Wada…

文献索引：Harada, Toshiro; Hayashiya, Toshio; Wada, Isao; Iwa-ake, Naoko; Oku, Akira Journal of the American Chemical Society, 1987 ,  vol. 109,  # 2  p. 527 - 532

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被引用次数: 70

摘要

Abstract: The enantioselective functionalization of a prochiral hydroxyl group in 2-substituted 1, 3-propanediols (HOCH2CR'R2CH20H) is presented. The reaction of the bis (trimethylsily1) derivative of the diol with I-menthone in the presence of trimethylsilyl trifluoromethanesulfonate selectively gave one of the diastereomers of the spiroketal in which the larger substituent (R') occupies an equatorial position. The equatorial spiroketal ...