Highly selective chemoenzymatic synthesis of enantiopure orthogonally protected trans-3-amino-4-hydroxypiperidines

Autor:	Ángela Villar-Barro, Rosario Brieva, Vicente Gotor
Rok vydání:	2015
Předmět:	biology Stereochemistry Organic Chemistry Absolute configuration Epoxide Regioselectivity biology.organism_classification Highly selective Biochemistry chemistry.chemical_compound Enantiopure drug chemistry Acetylation Biocatalysis Drug Discovery Organic chemistry Candida antarctica
Zdroj:	Tetrahedron. 71:6907-6912
ISSN:	0040-4020
DOI:	10.1016/j.tet.2015.07.014
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bc5b24d52681d13d36ca0f7f7a954a0e https://doi.org/10.1016/j.tet.2015.07.014 Zobrazit plný text záznamu Full Text from ScienceDirect