Journal
DALTON TRANSACTIONS
Volume 46, Issue 27, Pages 8763-8768Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6dt04612f
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Funding
- National Science Foundation [CHE-1362709]
- Margaret Strauss Kramer Graduate Fellowship (NYU)
- Global Research Initiative
- NYU
- NYU Florence
- S10 grant from the National Institutes of Health [OD016343]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1362709] Funding Source: National Science Foundation
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Silylenes are useful reactive intermediates for the stereoselective construction of compounds containing carbon-silicon bonds. Despite their synthetic utility, the development of either an enantioselective or diastereoselective metal-catalyzed silylene transfer reaction, in which ligands on the metal catalyst control stereoselectivity, has not been achieved. In this article, we report that the structure of the alkene is the most important for controlling stereoselectivity in these reactions. The stereochemical course of kinetically controlled silacyclopropanation reactions was not affected by the nature or chirality of the ligands on the metal. When silylene transfer reactions were reversible, however, products can be formed with a high degree of diastereoselectivity (90 : 10 d. r.).
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