Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 7, Pages 2350-2354Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200068q
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Funding
- Robert A. Welch Foundation [F-0038]
- NIH-NIGMS [RO1-GM069445]
- American Chemical Society Green Chemistry Institute Pharmaceutical Roundtable
- University of Texas at Austin, Center for Green Chemistry and Catalysis
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The cyclometalated iridium complex (S)-I derived from [Ir(cod)Cl](2), 4-cyano-3-nitrobenzoic acid, ally! acetate, and (S)-SEGPHOS is conveniently isolated by precipitation or through conventional silica gel flash chromatography. This single-component precatalyst allows alcohol mediated carbonyl crotylations to be performed at significantly lower temperature, resulting in enhanced levels of anti-diastereo- and enantioselectivity. Most significantly, the chromatographically isolated precatalyst (S)-I enables carbonyl crotylations that are not possible under previously reported conditions involving in situ generation of (S)-I.
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