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Article
Morita-Baylis-Hillman Reaction Inspired [3,3]-Rearrangement of Aryl Iodanes with α,β-Unsaturated Oxazolines
Zhi-Xiang Wang
University of Chinese Academy of Sciences
Corresponding Author
Bo Peng
Zhejiang Normal University
Corresponding Author
ORCiD: https://orcid.org/0000-0002-8237-6698
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This work is licensed under a CC BY 4.0 License. Read Full License
The [3,3]-rearrangement of aryl iodanes with α,β-unsaturated oxazolines has been developed by merging Morita-Baylis-Hillman (MBH) process into the rearrangement reaction. The method allows for the exclusively E-selective synthesis of a wide variety of valuable α-aryl α,β-unsaturated oxazolines which can be difficult to synthesize with other known methods. Experimental and computational mechanistic studies unraveled that the reaction proceeds via the assembly of both coupling partners followed by MBH-type addition to form rearrangement precursor, [3,3]-rearrangement, and stepwise E1cb-elimination. The E-selectivity of the reaction is favored both kinetically and thermodynamically.
Keywords
Morita-Baylis-Hillman Reaction, unsaturated oxazolines, [3,3]-Rearrangement, E1cb-elimination
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Article
Morita-Baylis-Hillman Reaction Inspired [3,3]-Rearrangement of Aryl Iodanes with α,β-Unsaturated Oxazolines
Zhi-Xiang Wang
University of Chinese Academy of Sciences
Corresponding Author
Bo Peng
Zhejiang Normal University
Corresponding Author
ORCiD: https://orcid.org/0000-0002-8237-6698
Badges
Prescreen
This manuscript passed our Prescreen assessment
Complete author information
Appropriate declaration statements
Potential risks to human health
Prescreen
History
CURRENT STATUS: Posted
Version 1
Posted 24 Aug, 2020
No community comments so far
Metrics
Comments: 0
PDF Downloads: ...
HTML Views: ...
Subject Areas
Organic Chemistry
License:
This work is licensed under a CC BY 4.0 License. Read Full License
The [3,3]-rearrangement of aryl iodanes with α,β-unsaturated oxazolines has been developed by merging Morita-Baylis-Hillman (MBH) process into the rearrangement reaction. The method allows for the exclusively E-selective synthesis of a wide variety of valuable α-aryl α,β-unsaturated oxazolines which can be difficult to synthesize with other known methods. Experimental and computational mechanistic studies unraveled that the reaction proceeds via the assembly of both coupling partners followed by MBH-type addition to form rearrangement precursor, [3,3]-rearrangement, and stepwise E1cb-elimination. The E-selectivity of the reaction is favored both kinetically and thermodynamically.
Figure 1
Figure 2
Figure 3
Figure 4