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One‐Pot Asymmetric Synthesis of Substituted Tetrahydrofurans via a Multicatalytic Benzoin/Michael/Acetalization Cascade
Author(s) -
He Gu,
Wu Fengbo,
Huang Wei,
Zhou Rui,
Ouyang Liang,
Han Bo
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.201400172
Subject(s) - chemistry , stereocenter , benzoin , stereoselectivity , iminium , yield (engineering) , michael reaction , cascade reaction , tetrahydrofuran , tandem , amine gas treating , organocatalysis , umpolung , stereochemistry , enantioselective synthesis , organic chemistry , combinatorial chemistry , catalysis , solvent , materials science , composite material , nucleophile , metallurgy
A sequential benzoin/Michael/acetalization tandem reaction catalyzed by NHC and amine together has been developed to assemble aromatic aldehydes and enals into chiral tetrahydrofuran derivatives bearing multiple functional groups and stereogenic centers with high stereoselectivity of up to 95:5 dr and 96% ee . The high yield and stereocontrol of this process may be due to both acid‐promoted symmetrization of racemic acyloins and iminium ion activation of enals.