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Synthesis 2011(12): 1859-1864  
DOI: 10.1055/s-0030-1260460
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Formation of Functionalized Cyclopentenes via Catalytic Asymmetric [3+2] Cycloaddition of Acrylamides with an Allenoate Promoted by Dipeptide-Derived Phosphines

Xiaoyu Han, Su-Xi Wang, Fangrui Zhong, Yixin Lu*
Department of Chemistry & Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore, Science Drive 3, Singapore 117543, Republic of Singapore
Fax: +6567791691; e-Mail: chmlyx@nus.edu.sg;
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Publication History

Received 18 March 2011
Publication Date:
05 May 2011 (online)

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Abstract

Acrylamides derived from 3,5-dimethyl-1H-pyrazole are employed in the asymmetric [3+2] cycloaddition with the allenoate, tert-butyl buta-2,3-dienoate, for the first time. d-Threonine-l-tert-leucine-based bifucntional phosphines are effective catalysts for the above reactions, affording regiospecific [3+2]-annulation products in excellent yields and with moderate enantioselectivities.

Key words

[3+2] cycloaddition - chiral phosphines - amino acids - bifunctional phosphine catalysts

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