Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 5, Pages 1498-1501Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b12960
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Funding
- National Natural Science Foundation of China [21325209, 21472205, 81521005]
- Program of Shanghai Academic Research Leader [14XD1404400]
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The first rhodium(I)-catalyzed enantioselective Si-H insertion reaction of alpha-diazoesters and alpha-diazophosphonates has been developed. The use of a C-1-symmetric chiral diene ligand enabled the asymmetric reaction to proceed under exceptionally mild conditions and give versatile chiral a-silyl esters and phosphonates with excellent enantioselectivities (up to 99% ee). The mechanism and stereothemical pathway of this novel Rh(I)-carbene-directed Si-H insertion was investigated by deuterium kinetic isotope effect experiments and DFT calculations.
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