Stereoselective acetalization of 1, 3-alkanediols by l-menthone: application to the resolution of racemic 1, 3-alkanediols and to the determination of the absolute …

…, Y Kagamihara, S Tanaka, A Inoue, A Oku

文献索引：Harada, Toshiro; Kurokawa, Hideaki; Kagamihara, Yasuhiro; Tanaka, Sachi; Inoue, Atsushi; Oku, Akira Journal of Organic Chemistry, 1992 , vol. 57, # 5 p. 1412 - 1421

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被引用次数: 37

摘要

A general and reliable method for the resolution of racemic 1, 3-&anediols, which involves their conversion into diastereomeric spiroacetah derived from l-menthone, ie deacrii. Thus, the reaction of the bis-O-trimethylsiyl derivatives of racemic 1, 3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel ...