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Enantioselective Construction of Spirooxindole Derivatives: Asymmetric [3+2] Cyclization of Isothiocyanatooxindoles with Allenic Esters or 2‐Butynedioic Acid Diesters
Author(s) -
Du Dan,
Jiang Yu,
Xu Qin,
Shi Min
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300460
Subject(s) - chemistry , enantioselective synthesis , cinchona , cycloaddition , organocatalysis , organic chemistry , hydrogen bond , cinchona alkaloids , catalysis , combinatorial chemistry , molecule
A novel Cinchona alkaloid‐derived organocatalyst having stronger hydrogen‐bonding donors that catalyzes the asymmetric [3+2] cycloaddition of 3‐isothiocyanatooxindoles with allenic esters or 2‐butynedioic acid diesters has been developed, affording functionalized spirooxindole derivatives in high yields along with good to excellent enantioselectivities under mild conditions. We also found that by changing the ratio of the substrates, different spirooxindole derivatives could be obtained in high yields along with good to excellent enantioselectivities.