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AM1 Transition State Modeling for the Enantioselectivities in the Chiral Oxazaborolidine‐Catalyzed Reductions of α‐ and β‐Aminoketones
Author(s) -
JianFen Fan,
YunXiang Lu,
QiuXia Wang,
LiFen Wu
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200590517
Subject(s) - chemistry , aminoketone , catalysis , transition state , state (computer science) , transition (genetics) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , algorithm , biochemistry , computer science , gene
AM1 transition state (TS) models were developed for the enantioselectivities in the reductions of α‐ and β‐aminoketones catalyzed by ( S )‐4‐benzyl‐5,5‐diphenyl‐1,3,2‐oxazaborolidine. The result showed that β‐aminoketone gave better enantioselectivity than its α‐analog. Different chiralities of the final products were obtained, R for the former and S for the latter. These semiempirical TS models are consistent with the experimental data.