Journal
ORGANIC LETTERS
Volume 14, Issue 9, Pages 2218-2221Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol300496v
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Funding
- American Chemical Society
- NIH/NIGMS [P41-GM0089153]
- 3M Nontenured faculty
- Bradford Borge Chemistry Fellowship
- U.S. Department of Education GAANN
- Achievement Rewards for College Scientists (ARCS)
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The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % Is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.
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