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Unexpected Selectivity in Sodium Borohydride Reductions of α-Substituted Esters: Experimental and Theoretical Studies

✍ Scribed by Liang-Chun Li; Ju-Xing Jiang; Jie Ren; Yi Ren; Charles U. Pittman Jr.; Hua-Jie Zhu

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 223 KB
Volume: 2006
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200500824

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✦ Synopsis

Abstract

The propensity of sodium borohydride to reduce the carbonyl group in eleven α‐substituted and two aromatic esters has been investigated by experiments and at the B3LYP/6‐31++G(d,p)//HF/6‐31G(d,p) level of theory. The chemoselectivities in nine of these reductions have been examined by experiments. Experimental results agree well with the calculated order of activation energies for hydride transfer to the ester carbonyl group. Methyl α‐bromoacetate reduces faster than methyl α‐fluoroacetate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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