Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 8, Pages 3050-3054Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob01268h
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Funding
- National Natural Science Foundation of China [21072102]
- Committee of Science and Technology of Tianjin
- State Key Laboratory of Elemento-Organic Chemistry of Nankai University
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An enantioselective Biginelli reaction has been developed by using a bifunctional primary amine-thiourea-TfOH (BPAT center dot TfOH) as a chiral phase-transfer catalyst and t-BuNH(2)center dot TFA as an additive in saturated brine at room temperature. The corresponding dihydropyrimidines were obtained in moderate-to-good yields with up to 99% ee under mild conditions. A plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.
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