Asymmetric synthesis of α-amino acids through α-iodination of chiral unsaturated carboxamides and stereoselective iodolactonization

Autor:	Norihiko Kikuchi, Tokushi Hanano, Takeo Taguchi, Osamu Kitagawa
Rok vydání:	1993
Předmět:	Chiral auxiliary Chemistry Stereochemistry Organic Chemistry Iodolactonization Enantioselective synthesis Halogenation Biochemistry Pyrrolidine chemistry.chemical_compound Drug Discovery Epimer Stereoselectivity Aliphatic compound
Zdroj:	Tetrahedron Letters. 34:2165-2168
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)60372-6
Popis:	The α-iodination reaction of chiral enamides 1 possessing (2R,5R)-2,5-bis(methoxymethyl)pyrrolidine as a chiral auxiliary proceeded with high diastereoselectivity in the presence of I 2 and s-collidine. The chiral iodides 2 thus obtained were converted to the α-BocNH-amides 3 without epimerization. The subsequent iodolactonization afforded trans-lactones 4 with a relatively high selectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::750396a6a67f08b43fa2be42533f78c2 https://doi.org/10.1016/s0040-4039(00)60372-6 Zobrazit plný text záznamu