Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 14, Pages 4948-4954Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b01986
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Funding
- NIH-NIGMS [R01 GM090007]
- Bristol-Myers Squibb
- A. P. Sloan Foundation
- Dreyfus Foundation
- Foote Family
- UCLA Gold Shield Alumnae
- UCLA Cota Robles Fellowship Program
- NSF [CHE-1048804]
- NIH NCRR [S10RR025631]
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We report synthetic methodology that permits access to two oxacyclic strained intermediates, the 4,5-benzofuranyne and the 3,4-oxacyclohexyne. In situ trapping of these intermediates affords an array of heterocyclic scaffolds by the formation of one or more new C-C or C-heteroatom bonds. Experimentally determined regioselectivities were consistent with predictions made using the distortion/interaction model and were also found to be greater compared to selectivities seen in the case of trapping experiments of the corresponding N-containing intermediates. These studies demonstrate the synthetic versatility of oxacyclic arynes and alkynes for the synthesis of functionalized heterocycles, while further expanding the scope of the distortion/interaction model. Moreover, these efforts underscore the value of harnessing strained heterocyclic intermediates as a unique approach to building polycyclic heteroatom-containing frameworks.
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