Volume 12, Issue 5-6 pp. 362-365
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Enantioresolution by the chiral phthalic acid method: Absolute configurations of substituted benzylic alcohols

Masashi Kosaka

Masashi Kosaka

Institute for Chemical Reaction Science, Tohoku University, Sendai, Japan

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Masataka Watanabe

Masataka Watanabe

Institute for Chemical Reaction Science, Tohoku University, Sendai, Japan

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Nobuyuki Harada

Corresponding Author

Nobuyuki Harada

Institute for Chemical Reaction Science, Tohoku University, Sendai, Japan

Institute for Chemical Reaction Science, Tohoku University, 2-1-1 Katahira, Aoba, Sendai 980-8577, JapanSearch for more papers by this author

Abstract

Substituted benzylic alcohols were enantioresolved by the chiral phthalic acid method as follows; 1) esterification of racemic alcohols with chiral phthalic acid, 2) separation of a diastereomeric mixture of the esters formed by HPLC on silica gel, and 3) recovery of enantiopure alcohols from the separated esters. The absolute configurations of chiral phthalic acid esters of benzylic alcohols were unambiguously determined by the X-ray crystallography using the campharsultam moiety as the internal standard of absolute configuration. Chirality 12:362–365, 2000. © 2000 Wiley-Liss, Inc.

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