Lewis Acid Mediated Asymmetric [2,3]-Sigmatropic Rearrangement of Allylic Amines. Scope and Mechanistic Investigation

Autor:	Peter Somfai, Pavel Tuzina, Jan Blid, Olaf Panknin
Rok vydání:	2007
Předmět:	Allylic rearrangement Reaction mechanism chemistry.chemical_compound Computational chemistry Chemistry Stereochemistry 2 3-sigmatropic rearrangement Organic Chemistry Enantioselective synthesis Lewis acids and bases Sigmatropic reaction Enantiomeric excess Triethylamine
Zdroj:	The Journal of Organic Chemistry. 72:1294-1300
ISSN:	1520-6904 0022-3263
Popis:	The first asymmetric [2,3]-sigmatropic rearrangement of achiral allylic amines has been realized by quaternization of the amines with an enantiomerically pure diazaborolidine and subsequent treatment with Et3N. The resultant homoallylic amines were obtained in good yields and excellent ee's. The observed diastereo- and enantioselectivities were rationalized by invoking a kinetically controlled process, and support for this model was obtained from an NMR spectroscopic investigation of the chiral Lewis acid-substrate complex. The structure of the Lewis acid-product complex was established by X-ray crystallographic analysis and supported the proposed mechanism.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c17df645995311fb8947bdb9e656a0fc https://doi.org/10.1021/jo062178v Zobrazit plný text záznamu