Ángela Villar-Barro, V. Gotor, R. Brieva
Sep 23, 2015
Citations
1
Influential Citations
8
Citations
Journal
Tetrahedron
Abstract
Abstract Optically pure orthogonally protected trans-3-amino-4-hydroxypiperidines have been easily prepared from (±)-1-benzyl-3,4-epoxypiperidine. The key steps are a regioselective epoxide ring-opening with diallylamine and the enzymatic resolution of the resulting aminoalcohol. It is remarkable the high enantioselectivity obtained with Candida antarctica lipase B in the acetylation of (±)-trans-1-benzyl-3-(diallylamino)-4-hydroxypiperidine. The versatility of the protecting groups is showed in the subsequent transformations performed in relation to the assignment of the absolute configuration of the products.