Highly Diastereoselective Alcoholysis of σ-Symmetric Dicarboxylic Acid Anhydrides Using 1-Phenyl-3,3-bis(trifluoromethyl)propan-1,3-diol
作者:Yoshimitsu Suda、Seiji Yago、Motoo Shiro、Takeo Taguchi
DOI:10.1246/cl.1992.389
日期:1992.3
Highly diastereoselective alcoholysis of σ-symmetric dicarboxylic acid anhydrides was performed using 1-phenyl-3,3-bis(trifluoromethyl)propan-1,3-diol. The importance of the geminally trifluoromethylated carbinol moiety for achieving a high degree of chiral induction was confirmed from lower diastereoselectivity with the hydroxyl protected 1,3-diol or with the similar 1,3-diols having hydrocarbon substituents instead of the trifluoromethyl group.
对σ对称二羧酸酐的高反应选择性醇解采用了1-苯基-3,3-二(三氟甲基)丙二醇。通过与羟基保护的1,3-二醇或具有碳氢取代基的相似1,3-二醇进行比较,确认了双氟甲基取代的羟醇部分在实现高程度的手性诱导中的重要性,因为后者的反应选择性较低。