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Origins of Stereoselectivity in Strain‐Release Allylations
Author(s) -
Zhang Xiyun,
Houk Kendall N.,
Leighton James L.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200462130
Subject(s) - stereoselectivity , trigonal bipyramidal molecular geometry , strain (injury) , aldehyde , transition state , chemistry , transition (genetics) , atom (system on chip) , stereochemistry , crystallography , catalysis , organic chemistry , biology , crystal structure , gene , computer science , anatomy , biochemistry , embedded system
Explaining the experiment : The transition states for a concerted asymmetric allylation (see scheme) were studied by theoretical methods. The apical attack of the aldehyde oxygen atom on Si accompanied by minimization of electrostatic repulsion in the trigonal‐bipyramidal transition state leads to high stereoselectivity.