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Chemistry. 2015 Mar 9;21(11):4224-8. doi: 10.1002/chem.201406475. Epub 2015 Jan 28.

Amino acid derived phosphine-catalyzed enantioselective 1,4-dipolar spiroannulation of cyclobutenones and isatylidenemalononitrile.

Author information

1
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663, N. Zhongshan Road, Shanghai, 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/main.jspy.

Abstract

Cyclobutenones have been explored as a new type of chiral 1,4-dipole four-carbon synthon, which readily undergoes organophosphine-mediated C-C bond cleavage and asymmetric intermolecular 1,4-dipolar spiroannulation with isatylidenemalononitrile in the presence of amino acid-derived chiral phosphine catalyst to furnish enantioenriched 3-spirocyclohexenone 2-oxindoles in good yield with up to 87% ee. To our knowledge, this is the first example of asymmetric transformation of cyclobutenones and the phosphine-catalyzed asymmetric 1,4-dipolar cycloaddition consisting of C-C bond activation is unprecedented.

KEYWORDS:

CC bond activation; organocatalysis; oxindoles; phosphanes; spiroannulation

PMID:
25630968
DOI:
10.1002/chem.201406475
[Indexed for MEDLINE]

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