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Asymmetric Organocatalytic Michael/Henry Domino Reactions through Hydrogen‐Bond Activation: Kinetic Access to Indane Scaffolds Bearing cis ‐Vicinal Substituents
Author(s) -
Loh Charles C. J.,
Atodiresei Iuliana,
Enders Dieter
Publication year - 2013
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.201302131
Subject(s) - indane , domino , bifunctional , chemistry , catalysis , vicinal , michael reaction , combinatorial chemistry , computer science , stereochemistry , medicinal chemistry , organic chemistry
Catalyst directs towards cis ! A bifunctional hydrogen‐bond‐catalyzed Michael/Henry domino reaction allows preferential asymmetric access to the kinetic cis ‐nitroindanol products with excellent enantioselectivity through a postulated matched transition state (see scheme; H‐Bo = hydrogen bond activation). This high yielding protocol opens up a new strategy to access highly useful enantio‐enriched cis ‐aminoindanol‐containing ligands and catalysts.