115346-82-2Relevant academic research and scientific papers
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 Configuration of Enantiomeric 1,3-Alkanediols
Harada, Toshiro,Kurokawa, Hideaki,Kagamihara, Yasuhiro,Tanaka, Sachi,Inoue, Atsushi,Oku, Akira
, p. 1412 - 1421 (2007/10/02)
A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described.Thus, the reaction of the bis-O-trimethylsilyl 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 column chromatography.Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol.An empirically derived correlation of configuration and 1H NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation.The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.
AN ENANTIODIFFERENTIATING CONVERSION OF RACEMIC 1,3-ALKANEDIOLS INTO ENANTIOMERICALLY PURE MATERIALS
Harada, Toshiro,Kurokawa, Hideaki,Oku, Akira
, p. 4847 - 4848 (2007/10/02)
Titanium tetrachloride promoted ring-cleavage reaction of a mixture of diastereomeric spiroketals derived from racemic 1,3-alkanediols and l-menthone, followed by benzoylation by Mitsunobu reaction, and the subsequent hydrolysis gave enantiomerically pure 1,3-alkanediols.
