Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 22, Pages 9982-9992Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c00078
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Funding
- 100 talent program of Chinese Academy of Sciences
- NSFC [21702217, 21572163, 21873074]
- 1000-Youth Talents Plan
- National Science & Technology Major Project Key New Drug Creation and Manufacturing Program China [2018ZX09711002-006]
- Shanghai-Technology Innovation Action Plan [18JC1415300]
- U.S. National Science Foundation [CHE-1764328]
- Shanghai-Youth Talent
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The efficient and stereoselective synthesis of polysubstituted butadienes, especially the multifunctional butadienes, represents a great challenge in organic synthesis. Herein, we wish to report a distinctive Pd(0) carbene-initiated decarboxylative olefination approach that enables the direct coupling of diazo esters with vinylethylene carbonates (VECs), vinyl oxazolidinones, or vinyl benzoxazinones to afford alcohol-, amine-, or aniline-containing 1,3-dienes in moderate to high yields and with excellent stereoselectivity. This protocol features operational simplicity, mild reaction conditions, a broad substrate scope, and gram-scalability. Notably, a structurally unique allylic Pd(II) intermediate was isolated and characterized. DFT calculation and control experiments demonstrated that a rare Pd(0) carbene intermediate could be involved in this reaction. Moreover, the polysubstituted butadienes as novel building blocks were unprecedentedly assembled into macrocycles, which efficiently inhibited the P-glycoprotein and dramatically reversed multidrug resistance in cancer cells by 190-fold.
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