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Chemistry. 2013 May 17;19(21):6739-45. doi: 10.1002/chem.201300204. Epub 2013 Mar 28.

Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates.

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1
Shanghai Key Laboratory of New Drug Design and School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China.

Abstract

The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (92-99 % ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary α-amino acid unit.

PMID:
23553867
DOI:
10.1002/chem.201300204
[Indexed for MEDLINE]
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