Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 31, Pages 9877-9884Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b04324
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Funding
- Scripps Research Institute
- NIH (NIGMS) [2R01GM084019]
- Austrian Science Foundation (FWF) [J 3424-N28]
- Asubio Pharma Co., Ltd.
- Austrian Science Fund (FWF) [J 3424] Funding Source: researchfish
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Pd-catalyzed C-H functionalization of mandelic acid and alpha-phenylglycine is reported. We have developed different protocols for the arylation, iodination, acetoxylation, and olefination of these substrates based on two different (Pd(II)/Pd(IV) and Pd(II)/Pd(0)) catalytic cycles. Four crucial features of these protocols are advantageous for practical applications. First, the alpha-hydroxyl and amino groups are protected with simple protecting groups such as acetates (Ac, Piv) and carbamates (Boc, Fmoc), respectively. Second, these protocols do not involve installation and removal of a directing group. Third, monoselectivity is accomplished. Fourth, no epimerization occurs at the vulnerable alpha-chiral centers.
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