Highly Selective Indium Mediated Allylation of Unprotected Pentosylamines

作者:Behr Jean Bernard*; Hottin Audrey; Ndoye Alpha
来源:Organic Letters, 2012, 14(6): 1536-1539.
DOI:10.1021/ol3002656

摘要

A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.

  • 出版日期2012-3-16