Asymmetric Access to α-Substituted Functional Aspartic Acid Derivatives by a [3+2] Strategy Employing a Chiral Dienophile

Autor:	Kawther Ben Ayed, Arnaud Martel, Jean-François Poisson, Houcine Ammar, Souhir Abid, Mathieu Y. Laurent, Gilles Dujardin, Anne Beauchard, Sandrine Py
Rok vydání:	2014
Předmět:	010405 organic chemistry Stereochemistry Chemistry Organic Chemistry Absolute configuration 010402 general chemistry Cleavage (embryo) 01 natural sciences 0104 chemical sciences 3. Good health Enantiopure drug Aspartic acid Side chain Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2014:2924-2932
ISSN:	1434-193X
Popis:	Enantiopure vinyl ethers of Stericol® underwent diastereoselective thermal 1,3 dipolar cycloadditions with N-benzyl, N-benzhydryl, and N-PMB aspartate ester nitrones. Chemoselective N-debenzylation of the resulting cycloadducts afforded diastereomerically and enantiomerically pure crystalline NH-isoxazolidine, the absolute configuration of which was established by X-ray crystallography. N-Protection and N–O cleavage of this isoxazolidine gave enantioenriched quaternary aspartate derivatives bearing functionalized side chains.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2a02aeea89a6577cdea51e6b21526066 https://doi.org/10.1002/ejoc.201301739 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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