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Synlett 2011(7): 1000-1004  
DOI: 10.1055/s-0030-1259709
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphine-Catalyzed [3+2] Cycloadditions of 2-Phenyl-4-Arylidene-5(4H)-Oxazolones with Allenoate: A Concise Synthesis of Aspartic Acid Analogues

You-Quan Zou, Chao Li, Jian Rong, Hao Yan, Jia-Rong Chen*, Wen-Jing Xiao*
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China
Fax: +86(27)67862041; e-Mail: wxiao@mail.ccnu.edu.cn;
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Publication History

Received 17 October 2010
Publication Date:
08 March 2011 (online)

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Abstract

A Ph3P-catalyzed [3+2] cycloaddition of 2-phenyl-4-arylidene-5(4H)-oxazolones with benzyl 2,3-butadienoate has been developed for the efficient synthesis of structurally diverse and conformationally constrained aspartic acid analogues.

Key words

cycloaddition - organocatalysis - phosphine - benzyl 2,3-butadienoate - aspartic acid analogues

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13

The configuration of 7a was determined by X-ray crystallographic analysis. CCDC 783340 (7a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

14

The relative stereochemistry of 10a was assigned by the coupling constants and NOE analysis of its NMR spectra, see the Supporting Information.