Tandem catalysis: Generating multiple contiguous carbon-carbon bonds through a ruthenium-catalyzed ring-closing metathesis/Kharasch addition
Tandem catalysis: Generating multiple contiguous carbon-carbon bonds through a ruthenium-catalyzed ring-closing metathesis/Kharasch addition
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DOI：
10.1021/ja055806j
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发表时间：
2005-11-23
影响因子：
15
通讯作者：
Snapper, ML
中科院分区：
文献类型：
--
作者：
Seigal, BA;Fajardo, C;Snapper, ML
Tandem catalysis can offer unique and powerful strategies for converting simple starting materials into more complex products in a single reaction vessel while generating less waste and minimizing handling. In this regard, Grubbs' ruthenium alkylidene (Cy3P)(2)Cl2Ru=CHPh is shown to catalyze two mechanistically distinct transformations to offer a unique protocol that effects multiple bond changes in a single operation. A tandem ruthenium-catalyzed olefin ring-closing metathesis (RCM)/Kharasch addition allows for the facile preparation of bicyclic [3.3.0], [4.3.0], and [5.3.0] ring systems in one step from the appropriately functionalized acyclic precursors. For substrates where the intramolecular Kharasch addition fails, an intermolecular Kharasch addition is possible. By combining the intra- and intermolecular Kharasch additions with RCM, three new contiguous carbon-carbon bonds with multiple stereocenters can be generated by the ruthenium catalyst in a controlled fashion in one operation through two mechanistically distinct pathways.
