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Preparative synthesis of the Corey chiral controller for enantioselective dihydroxylation of olefins

Preparative synthesis of the Corey chiral controller for enantioselective dihydroxylation of olefins A five-step synthesis of both enantiomers of 1,2-di(2,4,6-trimethylbenzylamino)-1,2-diphenylethane,i.e., Corey (R,R)- and (S,S)-controllers for enantioselective dihydroxylation of olefins by osmium tetroxide, starting from α,α′-diphenylglyoxime, has been developed. The key operations in the synthesis are the optical resolution of intermediaterac-1,2-diamino-1,2-diphenylethane into two enantiomers using only (R,R)-tartaric acid and the subsequent enhancement of the enantiomeric purity to >98% by crystallizations of the corresponding Schiff's bis-bases. Analysis of the enantiomeric purity of the controllers can be easily performed using1H NMR spectra of their salts with (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (MosherR-acid). http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Chemical Bulletin Springer Journals

Preparative synthesis of the Corey chiral controller for enantioselective dihydroxylation of olefins

Russian Chemical Bulletin , Volume 46 (1) – Aug 30, 2006

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References (9)

Publisher
Springer Journals
Copyright
Copyright © 1997 by Plenum Publishing Corporation
Subject
Chemistry; Chemistry/Food Science, general; Inorganic Chemistry; Organic Chemistry
ISSN
1066-5285
eISSN
1573-9171
DOI
10.1007/BF02495355
Publisher site
See Article on Publisher Site

Abstract

A five-step synthesis of both enantiomers of 1,2-di(2,4,6-trimethylbenzylamino)-1,2-diphenylethane,i.e., Corey (R,R)- and (S,S)-controllers for enantioselective dihydroxylation of olefins by osmium tetroxide, starting from α,α′-diphenylglyoxime, has been developed. The key operations in the synthesis are the optical resolution of intermediaterac-1,2-diamino-1,2-diphenylethane into two enantiomers using only (R,R)-tartaric acid and the subsequent enhancement of the enantiomeric purity to >98% by crystallizations of the corresponding Schiff's bis-bases. Analysis of the enantiomeric purity of the controllers can be easily performed using1H NMR spectra of their salts with (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid (MosherR-acid).

Journal

Russian Chemical BulletinSpringer Journals

Published: Aug 30, 2006

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