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Asymmetric [4+2] Annulations of Isatins with But‐3‐yn‐2‐one
Author(s) -
Wang Qiang,
Lian Zhong,
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.201300583
Subject(s) - chemistry , diethyl ether , catalysis , indoline , medicinal chemistry , organic chemistry , cinchona alkaloids , tartrate , solvent , pyran , enantioselective synthesis
The catalytic asymmetric [4+2] annulations of isatins with but‐3‐yn‐2‐one catalyzed by the Cinchona alkaloids‐derived oragnocatalyst (DHQD) 2 PHAL have been developed in the presence of 3.0 equivalents of D ‐diethyl tartrate in the mixed solvent (diphenyl ether/diethyl ether=1/1) or a slightly modified one, affording the corresponding substituted spiro[indoline‐3,2′‐pyran]‐2,4′(3′ H )‐diones in good to excellent yields with high enantioselectivities under mild conditions.