Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 12, Pages 5233-5240Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c00288
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Funding
- National Natural Science Foundation of China [21971254, 21821002, 92056103]
- Shanghai Rising-Star Program [19QA1411000]
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This study presents the catalytic sequential hydrosilylation of 1,3-enynes and 1,4-enynes promoted by cobalt complexes derived from bisphosphines. The reactions resulted in the formation of enantioenriched cyclic alkenylsilanes with simultaneous construction of a carbon-stereogenic center and a silicon-stereogenic center. The functionalization of these chiral silanes provides access to a variety of difficult-to-access chiral building blocks.
Catalytic sequential hydrosilylation of 1,3-enynes and 1,4-enynes promoted by cobalt complexes derived from bisphosphines are presented. Site- and stereoselective Si-H addition of primary silanes to 1,3-enynes followed by sequential intramolecular diastereo- and enantioselective Si-H addition afforded enantioenriched cyclic alkenylsilanes with simultaneous construction of a carbon-stereogenic center and a silicon-stereogenic center. Reactions of 1,4-enynes proceeded through sequential isomerization of the alkene moiety followed by site- and stereoselective hydrosilylation. A wide range of alkenylsilanes were afforded in high efficiency and selectivity. Functionalization of the enantioenriched silanes containing a stereogenic center at silicon delivered a variety of chiral building blocks that are otherwise difficult to access.
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