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  The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction:  Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols

List, B., Pojarliev, P., Biller, W. T., & Martin, H. J. (2002). The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction:  Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols. Journal of the American Chemical Society, 124(5), 827-833. doi:10.1021/ja0174231.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-A4CF-8 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-390B-D
Genre: Journal Article

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 Creators:
List, Benjamin1, Author           
Pojarliev, Peter1, Author
Biller, William T.1, Author
Martin, Harry J.1, Author
Affiliations:
1The Skaggs Institute for Chemical Biology and the Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA., ou_persistent22              

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 Abstract: We have developed proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines. Several of the studied reactions provide β-amino carbonyl compounds (Mannich products) in excellent enantio-, diastereo-, regio-, and chemoselectivities. The scope of each of the three components and the influence of the catalyst structure on the reaction are described. Reaction conditions have been optimized, and the mechanism and source of asymmetric induction are discussed. We further present application of our reaction to the highly enantioselective synthesis of 1,2-amino alcohols.

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Language(s): eng - English
 Dates: 2001-10-292002-01-102002-02-01
 Publication Status: Issued
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ja0174231
 Degree: -

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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 124 (5) Sequence Number: - Start / End Page: 827 - 833 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870