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An Ab Initio Study of Substituent Effects on the Electrocyclization of Silyloxyazadienes
Author(s) -
Bongini Alessandro,
Xia Zhining,
Panunzio Mauro
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700036
Subject(s) - substituent , chemistry , reactivity (psychology) , ab initio , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
The electrocyclization of 4‐substituted 3‐silyloxy‐2‐azadienes to β‐lactams was studied at the MP2/6‐31G* level of theory and the effect of the substituents on the reactivity of the azadiene and on the stereochemistry of the cyclic products was evaluated. It was shown that the electrocyclization is favoured when the substituent in 4‐position is in the ( Z ) configuration and discloses an electron‐donor effect. The cyclization reactions generally lead to trans β‐lactams, but with a basic substituent cis β‐lactams are obtained as well.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)