Asymmetric Organocatalytic Michael/Henry Domino Reactions through Hydrogen‐Bond Activation: Kinetic Access to Indane Scaffolds Bearing  cis ‐Vicinal Substituents | Zendy

Loh Charles C. J. | Zendy; Atodiresei Iuliana | Zendy; Enders Dieter | Zendy

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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.

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