Asymmetric aziridine synthesis by aza-Darzens reaction of N-diphenylphosphinylimines with chiral enolates. Part 1: Formation of cis-aziridines

Autor:	Andrew B. McLaren, Smita Thobhani, Alex A. Cantrill, Joseph B. Sweeney
Rok vydání:	2006
Předmět:	chemistry.chemical_compound chemistry Yield (chemistry) Aryl Organic Chemistry Drug Discovery Camphorsultam Imine Darzens reaction Organic chemistry Aziridine Biochemistry
Zdroj:	Tetrahedron. 62:3681-3693
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.01.068
Popis:	The aza-Darzens (‘ADZ’) reactions of N-diphenylphosphinyl (‘N-Dpp’) imines with chiral enolates derived from oxazolidinones and camphorsultam have been studied. Whilst oxazolidinone enolates reacted poorly in terms of aziridination, the use of the chiral enolate derived from both antipodes of N-bromoacetyl 2,10-camphorsultam, 2R-(5) and 2S-(5), with N-diphenylphosphinyl aryl and tert-butylimines proceeded in generally good yield to give, respectively, (2′R,3′R)- or (2′S,3′S)-cis-N-diphenylphosphinyl aziridinoyl sultams of high de.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::00750eff1ce4cf490ad115244e4f38a0 https://doi.org/10.1016/j.tet.2006.01.068 Zobrazit plný text záznamu Full Text from ScienceDirect