Regio-and stereoselective 6-exo-trig radical cyclisations onto chiral perhydro-1, 3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

R Pedrosa, C Andrés, JP Duque-Soladana…

Index: Pedrosa, Rafael; Andres, Celia; Duque-Soladana, Juan P.; Roson, Carlos D. Tetrahedron Asymmetry, 2000 , vol. 11, # 13 p. 2809 - 2821

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Citation Number: 23

Abstract

Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1, 3-benzoxazines derived from (−)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1, 5- hydrogen migration depends on the position of the acceptor double bond and the radical site.

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