A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes
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a-dual-cu-h-and-pd-catalyzed-stereoselective-synthesis-of-highly-substituted-1-3-dienes.pdf
Description
Submitted version
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1.52 MB
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Author(s)
Hou, Chuan-Jin
Schuppe, Alexander W.
Knippel, James Levi
Ni, Anton Z.
Buchwald, Stephen L.
Date Issued
November 2021
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Hou, Chuan-Jin, Schuppe, Alexander W, Knippel, James Levi, Ni, Anton Z and Buchwald, Stephen L. 2021. "A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes." Organic Letters, 23 (22).
Version
Original manuscript
Abstract
Conjugated dienes are versatile building blocks and prevalent substructures in synthetic chemistry. Herein, we report a method for the stereoselective hydroalkenylation of alkynes, utilizing readily available enol triflates. We leveraged an in situ-generated and geometrically pure vinyl-Cu(I) species to form the Z,Z- or Z,E-1,3-dienes in excellent stereoselectivity and yield. This approach allowed for the synthesis of highly substituted Z-dienes, including pentasubstituted 1,3-dienes, which are difficult to prepare by existing approaches.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.1c03324
