title: A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence.
abstract: (-)-(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.
authors.affiliation: Boston University, Department of Chemistry, Boston, Massachusetts 02215.
authors.forename: Kerrie L
authors.initials: KL
authors.lastname: Burgess
authors.forename: Neil J
authors.initials: NJ
authors.lastname: Lajkiewicz
authors.forename: Amitav
authors.initials: A
authors.lastname: Sanyal
authors.forename: Wanlin
authors.initials: W
authors.lastname: Yan
authors.forename: John K
authors.initials: JK
authors.lastname: Snyder