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  Chiral Brønsted Acids for Asymmetric Organocatalysis

Kampen, D., Reisinger, C. M., & List, B. (2010). Chiral Brønsted Acids for Asymmetric Organocatalysis. In B. List (Ed.), Topics in Current Chemistry, Vol. 291: Asymmetric Organocatalysis (pp. 395-456). Berlin Heidelberg: Springer Verlag.

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 Creators:
Kampen, Daniela1, Author              
Reisinger, Corinna M.1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: Asymmetric catalysis; BINOL; Dicarboxylic acids; N-Triflyl phosphoramides; Phosphoric acids; Strong chiral Brønsted acids
 Abstract: Chiral Brønsted acid catalysis is an emerging area of organocatalysis. Since the pioneering studies of the groups of Akiyama and Terada in 2004 on the use of chiral BINOL phosphates as powerful Brønsted acid catalysts in asymmetric Mannich-type reactions, numerous catalytic asymmetric transformations involving imine activation have been realized by means of this catalyst class, including among others Friedel-Crafts, Pictet-Spengler, Strecker, cycloaddition reactions, transfer hydrogenations, and reductive aminations. More recently, chiral BINOL phosphates found application in multicomponent and cascade reactions as for example in an asymmetric version of the Biginelli reaction. With the introduction of chiral BINOL-derived N-triflyl phosphoramides in 2006, asymmetric Brønsted acid catalysis is no longer restricted to reactive substrates. Also certain carbonyl compounds can be activated through these stronger Brønsted acid catalysts. In dealing with sensitive substrate classes, chiral dicarboxylic acids proved of particular value.

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Language(s): eng - English
 Dates: 2010
 Publication Status: Published in print
 Pages: 62
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1007/978-3-642-02815-1_1
 Degree: -

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Title: Topics in Current Chemistry, Vol. 291: Asymmetric Organocatalysis
Source Genre: Series
 Creator(s):
List, Benjamin1, Editor            
Affiliations:
1 Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585            
Publ. Info: Berlin Heidelberg : Springer Verlag
Pages: - Volume / Issue: 291 Sequence Number: - Start / End Page: 395 - 456 Identifier: ISBN: 978-3-642-02814-4