Title of article
A computational examination of Diels–Alder reactions with 1,3-cyclopentadienes bearing anionic and cationic substituents at C-5
Author/Authors
Xidos، نويسنده , , James D and Poirier، نويسنده , , Raymond A and Burnell، نويسنده , , D.Jean، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2000
Pages
4
From page
995
To page
998
Abstract
Ab initio calculations predict that deprotonation and protonation of 5-heterosubstituted 1,3-cyclopentadienes would significantly modify their facial selectivities in Diels–Alder additions. Anionic substituents enhance syn-addition, and cationic substituents promote anti-addition, relative to the neutral dienes. Stereoelectronic and steric effects together determine the facial selectivity of ionic dienes.
Keywords
cyclopentadienes , Diels–Alder reactions , steric and strain effects , Electronic effects
Journal title
Tetrahedron Letters
Serial Year
2000
Journal title
Tetrahedron Letters
Record number
1636365
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