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Stereoselective Formal Hydroamidation of Si-Substituted Arylacetylenes with DIBAL-H and Isocyanates: Synthesis of (E)- and (Z)-alpha-Silyl-alpha,beta-unsaturated Amides

Title
Stereoselective Formal Hydroamidation of Si-Substituted Arylacetylenes with DIBAL-H and Isocyanates: Synthesis of (E)- and (Z)-alpha-Silyl-alpha,beta-unsaturated Amides
Authors
Lee, HanseulCho, SoohongLee, YunmiJung, Byunghyuck
DGIST Authors
Jung, Byunghyuck
Issue Date
2020-10
Citation
Journal of Organic Chemistry, 85(19), 12024-12035
Type
Article
Article Type
Article
Keywords
ALKYNESCAFFEIC ACID-AMIDESALPHA,BETA-UNSATURATED AMIDESCATALYZED SYNTHESISCHIRAL AUXILIARYBOND FORMATIONAMINOCARBONYLATIONAVENANTHRAMIDESCARBONYLATIONREAGENTS
ISSN
0022-3263
Abstract
An efficient and stereoselective method for the synthesis of (E)- and (Z)-alpha-silyl-alpha,beta-unsaturated amides and its synthetic applications are presented herein. The solvent-controlled hydroaluminations of Si-substituted alkynes with DIBAL-H generate diastereomerically enriched alkenylaluminum reagents that are directly reacted with isocyanates at ambient temperature to afford alpha-silyl-alpha,beta-unsaturated amides in high yields with retained stereoselectivity. In particular, this process enables the synthesis of a broad range of (E)-alpha-silyl-alpha,beta-unsaturated amides, which are the less studied isomers. The synthetic utility of this method is highlighted by its short reaction time, ease of purification, easily accessible substrates and reagents, gram-scale synthesis, and the further transformations of C-Si bonds into C-H, C-X, and C-C bonds. © 2020 American Chemical Society.
URI
http://hdl.handle.net/20.500.11750/12813
DOI
10.1021/acs.joc.0c01903
Publisher
American Chemical Society
Related Researcher
  • Author Jung, Byunghyuck Asymmetric Organic Synthesis and Drug Synthesis Laboratory
  • Research Interests Organic Synthesis; Organo-transition metal chemistry; Catalytic Asymmetric Synthesis; Synthetic Methodologies; Synthesis of Natural Products and Drugs
Files:
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Collection:
Department of Emerging Materials ScienceAsymmetric Organic Synthesis and Drug Synthesis Laboratory1. Journal Articles


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