The chemistry phosphorus and sulfur ylides have been exploited for a facile, short and efficient synthesis of 3-spirocyclopentene- and 3-spiropyrazole-2-oxindoles from E- and Z-isomers of bromo derivatives of Morita-Baylis-Hillman adducts of isatin with Ph(3)P/activated alkene/K(2)CO(3) and Me(2)S/DEAD/K(2)CO(3), respectively, via [3 + 2]-annulation strategy.
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http://dx.doi.org/10.1039/b924066g | DOI Listing |
Chem Sci
December 2015
State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , P. R. China . Email:
The first regioselective catalytic asymmetric [3 + 2] cycloaddition of benzofuranone-derived olefins with allenoates and substituted allenoates has been developed in the presence of ()-SITCP, affording different functionalized 3-spirocyclopentene benzofuran-2-ones in good yields with high enantioselectivities under mild conditions. The substrate scope has also been examined. The regioselective outcomes for this phosphine-catalyzed [3 + 2] cycloaddition reaction can be rationalized using DFT calculations.
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April 2010
Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology, Trivandrum-695 019, Kerala, India.
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