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Updated: Aug 20, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
A new chiral anthracene for the asymmetric Diels-Alder/retro-Diels-Alder sequence
Kerrie L Burgess1, Neil J Lajkiewicz, Amitav Sanyal
1Boston University, Department of Chemistry, Boston, Massachusetts 02215.
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.
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