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Paper | Special issue | Vol 40, No. 1, 1995, pp.319-330
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S34
Diastereoselective Synthesis of Exo-6-aryl-3-azabicyclo[3.2.0]heptane Derivatives by Intramolecular [2+2]Photocycloadditions of Diallylic Amines

Gerd Steiner, Rainer Munschauer, Gerhard Klebe, and Lorenz Siggel

*Central Laboratory of BASF Aktiengesellschaft, D-67056 Ludwigshagen, Germany


N-Cinnamyl-N-allylamines (1) react upon irradiation with UV light via a photochemical [2+2] cycloaddition to give new exo-6-aryl-3-azabicyclo[3.2.0]heptanes (2) with high diastereoselectivity. A kinetic study as well as semiempirical quantum mechanical calculations support the proposed mechanism.