Journal
CHIRALITY
Volume 30, Issue 9, Pages 1096-1104Publisher
WILEY
DOI: 10.1002/chir.23003
Keywords
4-methylbenzoylthioureas; asymmetric Michael addition; Hartree-Fock calculations; nitroolefins; pyrazolin-5-ones
Funding
- Science and Technology Innovation Foundation of Shanxi Medical University [C01201009]
- Technology Innovation Team of Shanxi Province
- Program for the Top Science and Technology Innovation Teams of Higher Learning Institutions of Shanxi province
- Fund for Shanxi Key Subjects Construction
- Research Project Supported by Shanxi Scholarship Council of China [2017-061]
- Fund Program for the Scientific Activities of Selected Returned Overseas Professionals in Shanxi Province [2016]
- Natural Science Foundation of Shanxi Province [2015011104]
- National Natural Science Foundation of China [81473100]
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Cinchona alkaloid-derived 4-methyl/nitro benzoylthioureas were synthesized, which smoothly catalyzed the asymmetric Michael addition of pyrazolin-5-ones to nitroolefins. The results showed that electronic effects of substituents in the benzene ring of benzoylthioureas have subtle influences on their catalytic abilities and electron donating methyl group is favored than electron withdrawing nitro group. Preliminary Hartree-Fock calculations revealed that in the catalytic cycle, hydrogen bond energies of the complex formed with 4-methylbenzoylthioureas are about 0.19 to 1.56kcal/mol higher than with the corresponding 4-nitrobenzoylthioureas. 4-Methylbenzoylthioureas were identified as the most effective catalysts that promoted asymmetric Michael addition of pyrazolin-5-ones to nitroolefins to give the S- or R-products with high enantioselectivities.
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