SEMIEMPIRICAL CALCULATIONS ON THE MECHANISM OF STEREOSELECTIVE NABH4 REDUCTION OF 2-METHOXYCARBONYL-2-ALLYL-CYCLOPENTANONE

Authors
DESANTANNA CMR DEALENCASTRO RB BARREIRO EJ FRAGA CAM
Citation
Cmr. Desantanna et al., SEMIEMPIRICAL CALCULATIONS ON THE MECHANISM OF STEREOSELECTIVE NABH4 REDUCTION OF 2-METHOXYCARBONYL-2-ALLYL-CYCLOPENTANONE, Journal of molecular structure. Theochem, 340, 1995, pp. 193-199
Citations number
20
Categorie Soggetti
Chemistry Physical
Journal title
Journal of molecular structure. Theochem → ACNP
ISSN journal
01661280
Volume
340
Year of publication
1995
Pages
193 - 199
Database
ISI
SICI code
0166-1280(1995)340:<193:SCOTMO>2.0.ZU;2-C
Abstract
The stereoselective mechanism of reduction of 2-methoxycarbonyl-2-ally l-cyclopentanone with BH4- was investigated with the AM1 method in the gas phase. Geometries of reactants, transition states, and products w ere obtained for the reactions conducting to both trans and cis alkoxi des. The results suggest that the stereoselectivity is of steric origi n. The effect of a chelating Zn2+ ion on the reaction stereoselectivit y was analyzed.