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Asymmetric Synthesis of Bioxindole‐Substituted Hexahydrofuro[2,3‐ b ]furans via Hydroquinine Anthraquinone‐1,4‐diyl Diether‐Catalyzed Domino Annulation of Acylidenoxindoles/Isatins, Acylidenoxindoles and Allenoates
Author(s) -
Yang HaiBin,
Zhao Yunzhou,
Sang Rui,
Wei Yin,
Shi Min
Publication year - 2014
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.201400614
Subject(s) - annulation , chemistry , anthraquinone , domino , catalysis , steric effects , ring (chemistry) , stacking , cascade reaction , substrate (aquarium) , stereochemistry , combinatorial chemistry , organic chemistry , oceanography , geology
Abstract Hydroquinine anthraquinone‐1,4‐diyl diether [(DHQ) 2 AQN]‐catalyzed unprecedented asymmetric domino annulation reactions of acylidenoxindoles/isatins, acylidenoxindoles and allenoates are disclosed in this communication, providing a facile access to hexahydrofuro[2,3‐ b ]furans containing four contiguous chiral centers in good to excellent yields along with good to excellent ee values and moderate to good dr values. Based on theoretical investigations, a concerted [3+2] ring‐closure process was proposed, in which steric hindrance and π–π stacking interaction between catalyst and substrate subtly co‐control the diastereoselectivity of the reaction.