Pyrrolizidinone and indolizidinone synthesis: generation and intramolecular addition of. alpha.-acylamino radicals to olefins and allenes

DA Burnett, JK Choi, DJ Hart…

Index: Burnett, Duane A.; Choi, Joong-Kwon; Hart, David J.; Tsai, Yeun-Min Journal of the American Chemical Society, 1984 , vol. 106, # 26 p. 8201 - 8209

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Citation Number: 123

Abstract

Abstract: a-Acylamino radicals can be generated by treatment of phenylthio, methylthio, or phenylselenenyl lactams of type 7, 8, and 17 with tri-n-butyltin hydride in the presence of AIBN. The radicals add intramolecularly to olefins and allenes to give indolizidinones and pyrrolizidinones. The product distribution depends on the substitution patterns of the unsaturated moiety and the length of the chain connecting the radical and olefinic centers. ...