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Resolution of 1- and 2-naphthylmethoxyacetic acids, NMR reagents for absolute configuration determination, by use of L-phenylalaninol

✍ Scribed by Shoko Arita; Tetsuya Yabuuchi; Takenori Kusumi

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
96 KB
Volume
15
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

Racemic 1‐ and 2‐naphthylmethoxyacetic acids (1NMA and 2NMA), the chiral anisotropic reagents used for absolute configuration determination of chiral secondary alcohols and primary amines, were conveniently resolved to enantiomers (>99% ee) by condensation with L‐phenylalaninol (2‐amino‐3‐phenylpropanol), chromatographic separation of the diastereomers, and hydrolysis. This method enables large‐scale preparation of enantiomeric 1NMA and 2NMA. Chirality 15:609–614, 2003. © 2003 Wiley‐Liss, Inc.

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