In 4+2 cycloaddition, ENDO stereochemistry is preferred because:

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.53P
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In 4+2 cycloaddition, ENDO stereochemistry is preferred because: 
 
endo stereochemistry allows the diene to adopt s-cis conformation.
endo stereochemistry results in less steric hindrance.
the transition state leading to endo stereochemistry is higher energy.
it allows for additional π to π overlap between the diene and the dienophile. 
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