Enantioselective synthesis of 2-benzyloxy alcohols and 1, 2-diols via alkylation of chiral glycolate imides. A convenient approach to optically active glycerol derivatives

G Cardillo, M Oren, M Romero, S Sandri

文献索引：Cardillo, Giuliana; Orena, Mario; Romero, Marta; Sandri, Sergio Tetrahedron, 1989 , vol. 45, # 5 p. 1501 - 1508

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被引用次数: 43

摘要

The alkylation of the chiral enolates of glycolate imides 2a and 2b proceedes in highly diastereoselective manner to give 2'-substituted products in good yield. Reductive cleavage with LiBH4 affords the corresponding 2-benzyloxyalcohols 3a-c and 11a-b which are successively converted to 1, 2-diols in high optical purity. By this method (R)-1-propanoyloxy- 2, 3-propanediol 9 and (S)-1-tridecyloxy-2, 3-propanediol 14, a glyceride extracted from ...