Study of a Radical Cyclizations Cascade Leading to Bicyclo [3.1. 1] heptanes

S Bogen, L Fensterbank, M Malacria

Index: Bogen, Stephane; Fensterbank, Louis; Malacria, Max Journal of Organic Chemistry, 1999 , vol. 64, # 3 p. 819 - 825

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Citation Number: 39

Abstract

An efficient radical cascade involving a 5-exo-dig, a 1, 6-H transfer, a 6-endo-trig, a 4-exo- dig, and a final 1, 6-H transfer allows the diastereoselective construction of bicyclo [3.1. 1] heptanes. The size of the R substituent at the propargylic position governs the diastereoselectivity of the 6-endo-trig step. Other parameters (acetylenic substituents, unsaturated partners,...) have been investigated, and the scope and the limitations of the ...