期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 7, 页码 1968-1972出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309430
关键词
alkenes; olefin metathesis; ring-opening; cross-metathesis; ruthenium; synthetic methods
资金
- NSF [CHE-1111074]
- AstraZeneca
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1362763] Funding Source: National Science Foundation
A broadly applicable Ru-catalyzed protocol for Z-selective ring-opening/cross-metathesis (ROCM) is disclosed. In addition to reactions relating to terminal alkenes of different sizes, the first examples of Z-selective ROCM processes involving heteroaryl olefins, 1,3-dienes, and O- and S-substituted alkenes as well as allylic and homoallylic alcohols are reported. Z-Selective transformations with an -substituted allylic alcohol are shown to afford congested Z alkenes with high diastereoselectivity. Transformations are performed in the presence of 2.0-5.0mol% of a recently disclosed Ru-based dithiolate complex that can be easily prepared in a single step from commercially available starting materials. Typically, transformations proceed at ambient temperature and are complete within eight hours; products are obtained in up to 97% yield, >98:2 Z/E, and >98:2 diastereomeric ratio. The present investigations reveal a mechanistically significant attribute of the Ru-based dithiolates that arises from electrostatic interactions with anionic S-based ligands.
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