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Amino Acid Derived Phosphine‐Catalyzed Enantioselective 1,4‐Dipolar Spiroannulation of Cyclobutenones and Isatylidenemalononitrile
Author(s) -
Li Yangyan,
Su Xiao,
Zhou Wei,
Li Wenbo,
Zhang Junliang
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406475
Subject(s) - synthon , enantioselective synthesis , phosphine , catalysis , chemistry , yield (engineering) , stereochemistry , cycloaddition , organic chemistry , medicinal chemistry , materials science , metallurgy
Cyclobutenones have been explored as a new type of chiral 1,4‐dipole four‐carbon synthon, which readily undergoes organophosphine‐mediated CC 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 CC bond activation is unprecedented.