Journal
CHEMICAL SCIENCE
Volume 12, Issue 18, Pages 6406-6412Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc00972a
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Funding
- National Key R&D Program of China [2019YFE0109200]
- NSFC [U1702286]
- China Postdoctoral Science Foundation [2019M663581]
- NSF of Yunnan Province [2019FY003010, 2019FI018]
- Program for Yun-Ling Scholars
- IRTSTYN
- US National Science Foundation [CHE-1902509]
- [202005AB160003]
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This study introduces a unique enantioselective nickel-catalyzed vinylation method for the synthesis of diverse vinyl aryl methyl amines and enantioenriched 1,3-diamine derivatives, which are frequently found in natural products and medications. The success of this method relies on a Ni/chiraphos catalyst system and a less reducing 2-azaallyl anion, enabling an anionic vinylation route over a background radical reaction. Scalability and synthetic potential of this method are confirmed through a telescoped gram scale synthesis and product derivatization study.
A unique enantioselective nickel-catalyzed vinylation of 2-azaallyl anions is advanced for the first time. This method affords diverse vinyl aryl methyl amines with high enantioselectivities, which are frequently occurring scaffolds in natural products and medications. This C-H functionalization method can also be extended to the synthesis of enantioenriched 1,3-diamine derivatives by employing suitably elaborated vinyl bromides. Key to the success of this process is the identification of a Ni/chiraphos catalyst system and a less reducing 2-azaallyl anion, all of which favor an anionic vinylation route over a background radical reaction. A telescoped gram scale synthesis and a product derivatization study confirmed the scalability and synthetic potential of this method.
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