Inside-outside stereoisomerism. 5. Synthesis and reactivity of trans-bicyclo [n. 3.1] alkanones prepared via the intramolecular photocycloaddition of dioxenones

JD Winkler, BC Hong, JP Hey…

Index: Winkler, Jeffrey D.; Hong, Bor-Cherng; Hey, John P.; Williard, Paul G. Journal of the American Chemical Society, 1991 , vol. 113, # 23 p. 8839 - 8846

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Citation Number: 18

Abstract

Abstract: The stereoselectivity of the intramolecular photocycloaddition of a series of bicyclic dioxenones has been examined. The selective formation of trans-fused photoadducts is observed in almost all cases, which upon fragmentation lead to the synthesis of bicycloalkanones with an'inside-outside" or trans intrabridgehead stereochemical relationship. This methodology has been applied to the synthesis of several'inside-outside ...