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

P. Veeraraghavan Ramachandran, Sanjay V. Malhotra, Herbert C. Brown

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

While o-hydroxyaceto- and -benzophenones undergo reduction with B-chlorodiisopinocampheylborane (1) and diisopinocampheylborane (2) at the same rate, the reduction of o-carboxyaceto- and -benzophenones is faster 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-aminoaceto- and -benzophenone undergo faster reduction with 1 and 2. The rate enhancing influence of HCl and MeSO3H on the intramolecular asymmetric reduction of these amino ketones with 2 has been tested and confirmed.

Original languageEnglish (US)
Pages (from-to)957-960
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number6
DOIs
StatePublished - Feb 10 1997
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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