Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 10001-10014Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01378
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Funding
- CONICET [PUE-2016]
- ANPCyT [PICT.2014-0408]
- Agencia Santafesina de Ciencia, Tecnica e Innovation (ASACTEI) [AC-2015-00005]
- Universidad Nacional de Rosario [BIO 426, BIO 514]
- CONICET
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The transition-metal-catalyzed [2 + 2 + 2]-cycloaddition of alkynes has become a powerful atom-economical strategy for aromatic ring construction. Unfortunately, the control of the stereo-, regio-, and chemoselectivity of these processes is usually challenging, and these reactions can potentially lead to complex unuseful mixtures. While solid-phase chemistry has proven to be a successful tool for decreasing the number of cycloadducts formed and for facilitating the purification step, an integral use of the out-coming products in this complex reaction is described herein. By using an immobilized monoalkyne, the transition-metal-catalyzed [2 + 2 + 2]-cycloaddition with soluble 1,6-diyne-esters led to the simultaneous preparation of soluble and solid-supported phthalides, showing a new way to benefit from solid-phase synthetic methodologies.
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