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。