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  The Catalytic Acylcyanation of Imines

Pan, S. C., & List, B. (2008). The Catalytic Acylcyanation of Imines. Chemistry – An Asian Journal, 3(2), 430-437. doi:10.1002/asia.200700327.

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 Creators:
Pan, Subhas Chandra1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: acylcyanation; enantioselectivity; imines; multicomponent reactions; organocatalysis
 Abstract: The catalytic acylcyanation of aldimines with acylcyanides and a direct three‐component variant involving the generation of an imine in situ have been developed. Furthermore, a highly enantioselective version has been established, culminating in the first organocatalytic asymmetric three‐component Strecker reaction. Jacobsen thiourea catalysts were found to catalyze the reaction with excellent enantioselectivities, whereas binol phosphates (binol=1,1′‐bi‐2,2′‐naphthol) proved to be catalytically active but only modestly enantioselective. A large number of different substrates could be used in the processes described, thus illustrating the potential of our reaction for the generation of diversity within the attractive α‐amino carbonyl framework. Furthermore, a novel cyclic amidine was obtained from the reaction of acetyl cyanide with ketimines.

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Language(s): eng - English
 Dates: 2007-09-282008-01-292008-02-01
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/asia.200700327
 Degree: -

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Title: Chemistry – An Asian Journal
  Abbreviation : Chem. – Asian J.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 3 (2) Sequence Number: - Start / End Page: 430 - 437 Identifier: ISSN: 1861-4728
CoNE: https://pure.mpg.de/cone/journals/resource/1000000000223780