Studies on the Stereoselectivity of Pinacol Coupling Reaction Mediated by TiCl4-Mg

Abstract

Abstract: TiCl₄-Mg and TiCl₄-Mg-TMEDAsystems are used as reagents of pinacol coupling reaction, thus reductive coupling of aromatic aldehydes with a high stereoselectivity. The observed stereochemistry of the reaction is briefly discussed in term of Ti-bridging controlled models. Three kinds of chiral auxiliary 1,4-diamines, 1,4-diphosphines and 1,4-diethers, are used in the pinacol formation reaction of benzaldehyde mediated by TiCl₄-Mg, and hydrobenzoin was obtained with ee 50% of (R,R)-isomer. when N,N,N',N'-tetramethyl-2,3-O-isopropylidene-2,3-dihydroxy, 1,4-butanediamine was used as chiral modifier.

Key words: Pinacol coupling reaction, Aromatic aldehydes, Titanium tetrachloride-magnesium, Stereoselectivity, Enantioselectivity

CLC Number:

O621.25

TrendMD:

LI Ting-You, WANG Li-Ping, ZHANG Tao, LI Yao-Xian, WANG Zong-Mu. Studies on the Stereoselectivity of Pinacol Coupling Reaction Mediated by TiCl₄-Mg[J]. Chem. J. Chinese Universities, 2000, 21(9): 1391.

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Studies on the Stereoselectivity of Pinacol Coupling Reaction Mediated by TiCl₄-Mg

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