Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 16, Pages 5916-5921Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja101909t
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Funding
- Scripps Research Institute
- National Institutes of Health (NIGMS) [1 R01 GM084019-01A1]
- NSF
- U.S. Department of Defense
- Skaggs-Oxford Scholarship
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A novel Pd(II)-catalyzed ortho-C-H olefination protocol has been developed using spatially remote, unprotected tertiary, secondary, and primary alcohols as the directing groups. Mono-N-protected amino acid ligands were found to promote the reaction, and an array of olefin coupling partners could be used. When electron-deficient alkenes were used, the resulting olefinated intermediates underwent subsequent Pd(II)-catalyzed oxidative intramolecular cyclization to give the corresponding pyran products, which could be converted into ortho-alkylated alcohols under hydrogenolysis conditions. The mechanistic details of the oxidative cyclization step are discussed and situated in the context of the overall catalytic cycle.
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