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  Asymmetric Disulfonimide-Catalyzed Synthesis of δ-Amino-β-Ketoester Derivatives by Vinylogous Mukaiyama–Mannich Reactions

Wang, Q., van Gemmeren, M., & List, B. (2014). Asymmetric Disulfonimide-Catalyzed Synthesis of δ-Amino-β-Ketoester Derivatives by Vinylogous Mukaiyama–Mannich Reactions. Angewandte Chemie International Edition, 53(49), 13592-13595. doi:10.1002/anie.201407532.

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 Creators:
Wang, Qinggang1, Author              
van Gemmeren, Manuel1, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: δ-amino-β-ketoesters; disulfonimides; organocatalysis; vinylogous Mukaiyama–Mannich reaction
 Abstract: An organocatalytic asymmetric synthesis of δ-amino-β-ketoester derivatives has been developed. A chiral disulfonimide (DSI) serves as a highly efficient precatalyst for a vinylogous Mukaiyama–Mannich reaction of readily available dioxinone-derived silyloxydienes with N-Boc-protected imines, delivering products in excellent yields and enantioselectivities. The synthetic utility of this reaction is illustrated in various transformations, including a new C-C bond-forming reaction, which provide useful enantioenriched building blocks. The methodology is applied in a formal synthesis of (−)-lasubin.

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Language(s): eng - English
 Dates: 2014-10-272014-12-01
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201407532
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 53 (49) Sequence Number: - Start / End Page: 13592 - 13595 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851