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One‐Pot Synthesis of Pentasubstituted Cyclohexanes by a Michael Addition Followed by a Tandem Inter–Intra Double Henry Reaction
Author(s) -
García Ruano José Luis,
Marcos Vanesa,
Suanzes Juan Antonio,
Marzo Leyre,
Alemán José
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900894
Subject(s) - cyclohexanes , michael reaction , tandem , reagent , chemistry , intramolecular force , cascade reaction , catalysis , nitroaldol reaction , addition reaction , organic chemistry , enantioselective synthesis , composite material , materials science
Michael, Henry, and Henry : A new one‐pot reaction of α,β‐unsaturated aldehydes and β‐dicarbonyls, which involves a Michael reaction catalyzed by diarylprolinol ethers and an inter–intramolecular Henry tandem reaction catalyzed by TBAF (see scheme), has been developed. The reaction proceeds in high enantio‐ and diastereoselectivity for a wide range of unsaturated aldehydes and β‐dicarbonyl reagents.