Combined computational and experimental investigations on the diastereoselective hydrogenation of steroids by chiral oxazaborolidine

Gy Göndös, I. Pálinkó

Research output: Contribution to journalConference article

3 Citations (Scopus)

Abstract

In this work the results of semiempirical quantum chemical calculations are described that support experimental findings applying the methyl derivative of oxazaborolidine-BH3 chiral complex for the reduction of a number of pregnane derivatives (3α-hydroxy-5β-pregnane-20-one,3α,17α-dihydroxy-5β-p regnane-20-one, 3α,21-dihydroxy-5β-pregnane-20-one, and 3α,17α,21-trihydroxy-5β-pregnane-20-one). Calculations were performed by the MNDO method. The reactants, the products, the assumed transition states, as well as the assumed intermediate structures were optimized without any constraints. Calculations were able to reproduce the observed activity sequence and explain the experimental finding that the thermodynamically less stable isomer is formed preferentially.

Original languageEnglish
Pages (from-to)253-258
Number of pages6
JournalInternational Journal of Quantum Chemistry
Volume84
Issue number2
DOIs
Publication statusPublished - Aug 5 2001
Event3th European Conference on Computational Chemistry (EUCO-CC3) - Budapest, Hungary
Duration: Sep 4 2000Sep 8 2000

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Keywords

  • Chiral methyl-oxazaborolidine
  • MNDO method
  • Pregnane derivatives
  • Reduction
  • Semiempirical quantum chemical calculations

ASJC Scopus subject areas

  • Atomic and Molecular Physics, and Optics
  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

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