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Stereoselective reduction of benzoin by the NADH model 3-(dimethylcarbamoyl)-1,2,4-trimethyl-1,4-dihydropyridine

✍ Scribed by Nicoline A. Beijer; Jozef A. J. M. Vekemans; Henk M. Buck

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 228 KB
Volume: 109
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19901090708

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✦ Synopsis

Abstract

The Mg(ClO~4~)~2~‐induced reduction of racemic benzoin by the racemic NADH model compound 3‐(dimethylcarbamoyl)‐1,2,4‐trimethyl‐1,4‐dihydropyridine (1), in accordance to Cram's rule, leads exclusively to meso‐1,2‐diphenyl‐1,2‐ethanediol. However, while R‐1 equally reduces 5‐benzoin to afford meso‐1,2‐diphenyl‐1,2‐ethanediol, S‐1 is reluctant to react with S‐benzoin. The intermediacy of a strictly organized transition state, composed of chelated substrate, dihydropyridine and magnesium ion is involved.

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