Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines

Autor:	Ryan R. Walvoord, Marisa C. Kozlowski
Rok vydání:	2015
Předmět:	biology Aryl Organic Chemistry Enantioselective synthesis Cinchona biology.organism_classification Biochemistry Catalysis Stereocenter chemistry.chemical_compound Enantiopure drug chemistry Drug Discovery Organic chemistry Epimer Selectivity
Zdroj:	Tetrahedron Letters. 56:3070-3074
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2014.12.105
Popis:	Inexpensive and readily available cinchonidinium acetate is an effective catalyst for the syn-selective aza-Henry reaction of arylnitromethanes and aryl imines. The resulting masked cis-stilbenediamine products are produced in excellent diastereoselectivity and good enantioselectivity, and enantiopure material can be achieved via recrystallization. The features of the cinchona catalyst needed for selectivity are discussed, with specific emphasis on formation of a kinetically controlled syn-product without epimerization of the highly acidic α-nitro stereocenter.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::00ca14a1bbdb4a70c4b453fa064c0438 https://doi.org/10.1016/j.tetlet.2014.12.105 Zobrazit plný text záznamu Full Text from ScienceDirect