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

作者：Ben Ayed Kawther; Beauchard Anne; Poisson Jean Francois; Py Sandrine; Laurent Mathieu Y; Martel Arnaud; Ammar Houcine; Abid Souhir; Dujardin Gilles^*

来源：European Journal of Organic Chemistry, 2014, 2014(14): 2924-2932.

DOI：10.1002/ejoc.201301739

• Asymmetric synthesis
• Cycloaddition
• Amino acids
• Heterocycles

Enantiopure vinyl ethers of Stericol((R)) 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.

• 出版日期2014-5