Highly selective indium mediated allylation of unprotected pentosylamines
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.
Behr, Jean-Bernard,Hottin, Audrey,Ndoye, Alpha
supporting information; experimental part
p. 1536 - 1539
(2012/05/19)
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