Synthesis

Preparation of chiral building blocks for a highly convergent vitamin E synthesis. Systematic investigations on the enantioselectivity of the Sharpless bishydroxylation

LF Tietze, J Görlitzer

Index: Tietze, Lutz F.; Goerlitzer, Jochen Synthesis, 1998 , # 6 p. 873 - 878

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Citation Number: 12

Abstract

Abstract: The enantioselective bishydroxylation of protected 2-methylprop-2-enol 15 and 3- methylbut-3-en-1-ol 16 to give the corresponding diols 18 and 19, respectively, which can be transformed into building blocks for the synthesis of natural vitamin E, is described. It is shown that the enantioselectivity of the bishydroxylation reaction clearly depends on the type of protecting group and its distance from the alkene moiety, with 96% ee for 16a and ...

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