Asymmetric alkylation mediated by tricyclic chiral sultam auxiliaries

Autor:	Albert W. M. Lee, Wai Yeung Wong, Jing Lin, Wing Hong Chan
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Organic Chemistry Halide Sodium hexamethyldisilazide Alkylation Biochemistry Medicinal chemistry Kinetic resolution Deprotonation chemistry Drug Discovery lipids (amino acids peptides and proteins) Alkyl Tricyclic
Zdroj:	Tetrahedron. 55:13983-13998
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(99)00872-8
Popis:	The use of enantiomerically pure sultams (+)-1 and (−)-1 as practical chiral auxiliaries for asymmetric alkylation reactions is described in full. Deprotonation of the N-acylated products derived from the auxiliaries with sodium hexamethyldisilazide followed by treatment with alkyl halides gave products with high diastereoselectivity. On treatment with excess racemic α-bromopropanoate or α-bromobutanoate, the enolates of the corresponding N-acyl sultam underwent highly diastereoselective alkylations to afford products with a complete absolute control of two contiguous chiral centres.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::aa7d98f4c4666971b474688be2229aef https://doi.org/10.1016/s0040-4020(99)00872-8 Zobrazit plný text záznamu Full Text from ScienceDirect