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Combined computational and experimental investigations on the diastereoselective hydrogenation of steroids by chiral oxazaborolidine
Author(s) -
Göndös Gy.,
Pálinkó I.
Publication year - 2001
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.1328
Subject(s) - pregnane , mndo , chemistry , computational chemistry , quantum chemical , sequence (biology) , quantum chemistry , reduction (mathematics) , derivative (finance) , stereochemistry , molecule , organic chemistry , reaction mechanism , mathematics , geometry , catalysis , biochemistry , financial economics , economics
In this work the results of semiempirical quantum chemical calculations are described that support experimental findings applying the methyl derivative of oxazaborolidine‐BH 3 chiral complex for the reduction of a number of pregnane derivatives (3α‐hydroxy‐5β‐pregnane‐20‐one, 3α,17α‐dihydroxy‐5β‐pregnane‐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. © 2001 John Wiley & Sons, Inc. Int J Quantum Chem 84: 253–258, 2001