Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 4, Pages 2048-2058Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02787
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Funding
- National Natural Science Foundation of China [21702218, 81973166, 91753207]
- National Science and Technology Major Project major new drug creation [2018ZX09711002-006, 2018ZX09711002-007]
- 1000-Youth Talents Plan
- Youth Innovation Promotion Association [2017333]
- K. C. Wong Education Foundation
- Science and Technology Commission of Shanghai Municipality [18431907100]
- Shanghai Rising-Star Program [17QA1405000]
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Ortho C-H allenylation of electron-rich benzene derivatives with propargylic alcohol derivatives has been a challenge, due to their great innate tendency toward a para C-H allenylation via an SN2'-type substitution process. Here, we described a Ru(II)-catalyzed regioselective ortho C-H allenylation of electron-rich aniline and phenol derivatives, which allows the previously challenging synthesis of a broad range of ortho allenylated aniline and phenol derivatives. More significantly, highly optically active fully substituted allenes can also be prepared with high enantiomeric excess via a highly efficient chirality transfer. No para C-H allenylation product was observed in the current catalytic system, thus showing a complete reversibility of the regioselectivity.
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