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Stereoselective Yang Reactions: a Three-Stage Selection Model#

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image of Research on Chemical Intermediates

The photocyclization of triplet excited α-acylamino-substituted alkyl tolyl ketones 1a-d in nonpolar solvents was studied with emphasis on the three selection steps which are relevant for Yang reactions: (A) the γ-hydrogen abstraction, (B) triplet biradical dynamics, and (C) spin-orbit coupling (SOC) controlled intersystem crossing (ISC). The competition between cleavage and bond formation is controlled by conformational changes at the triplet biradical stage which favor or disfavor close-contact SOC geometries. The relative configurations of products 2a-d were determined by NMR and X-ray structure analyses (for 2c). The valine-derived substrate 1c was channeled through steps (A) and (B) to give with high stereoselectivity the cyclobutanol 2c. The isoleucine-derived substrates were applied as (2RS,3S)-1d and as the enantiomerically pure (2S,3S)-1d, uncovering stereospecificity which originate from differences in triplet biradical conformations.

Affiliations: 1: Institut für Organische Chemie der Universität zu Köln, Greinstr. 4, D-50939 Köln, GERMANY


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