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Rate enhancing effect of hydrogen chloride and methanesulfonic acid on the intramolecular asymmetric reduction of 0-aminoaceto- and -benzophenones with diisopinocampheylborane

✍ Scribed by P.Veeraraghavan Ramachandran; Sanjay V Malhotra; Herbert C Brown

Book ID: 104256234
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 273 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02489-6

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✦ Synopsis

While o-hyclroxyaceto-and -benzophenones undergo reduction with Behlorodiisopinoeampheyiborane (1) and diisopinoeampbeylborane (2) at the same rate, the reduction of o-carboxyaceto-and -benzopbenones Is fast~ with 2 as compared with 1. The rate retardation for the reaction of keto acids with 1 was accounted by a competition between an intra-and intermolecular reduction. In contrast, o-aminoaeeto-and -benzophenone undergo faste~ reduction with 1 than with 2. The rate enhancing influence of HCI and MeSO3H on the intramoleeular asymmetric reduction of these amino ketones with 2 has been tested and confirmed.

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