A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence.
(-)-(R)-9-(1,2-Dimethoxyethyl)anthracene (8) is successfully employed as a chiral template in the Diels-Alder/retro-Diels-Alder sequence for the preparation of alpha,beta-unsaturated lactams. The cycloadditions proceed with complete diastereoselectivity, and regioselectivity in subsequent transformations of the carbonyl groups is also excellent. Flash vacuum pyrolysis accomplishes the cycloreversion.
Burgess
Kerrie L
KL
Boston University, Department of Chemistry, Boston, Massachusetts 02215.
Lajkiewicz
Neil J
NJ
Sanyal
Amitav
A
Yan
Wanlin
W
Snyder
John K
JK