A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols

Autor:	Claude Agami, Gwilherm Evano, François Couty
Rok vydání:	2002
Předmět:	Inorganic Chemistry chemistry.chemical_compound Enantiopure drug Nitrile Chemistry Organic Chemistry Organic chemistry Alcohol Stereoselectivity Physical and Theoretical Chemistry Alkylation Ring (chemistry) Catalysis
Zdroj:	Tetrahedron: Asymmetry. 13:297-302
ISSN:	0957-4166
Popis:	Enantiopure 2-cyano azetidines were prepared in high yields from β-amino alcohols. This synthesis was shown to be general and is based on two important steps: (i) chlorination of a N-cyanomethylated β-amino alcohol and (ii) a 4-exo-trig ring closure through the alkylation of a lithiated α-amino nitrile. The former step is stereoselective when ephedrine-derived β-amino alcohols are used. In the case of a phenylglycinol-derived β-amino alcohol, this step also involves a rearrangement.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2581171567d1e3c3b092778eb88146d4 https://doi.org/10.1016/s0957-4166(02)00076-9 Zobrazit plný text záznamu Full Text from ScienceDirect