Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction
Chauhan, P., Mahajan, S., Kaya, U., Peuronen, A., Rissanen, K., & Enders, D. (2017). Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction. Journal of Organic Chemistry, 82(13), 7050-7058. https://doi.org/10.1021/acs.joc.7b01113
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Journal of Organic ChemistryAuthors
Date
2017Discipline
Epäorgaaninen ja analyyttinen kemiaOrgaaninen kemiaNanoscience CenterInorganic and Analytical ChemistryOrganic ChemistryNanoscience CenterCopyright
© 2017 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.
A new series of N-Boc ketimines derived from pyrazolin-5-ones have been used as electrophiles in asymmetric Mannich reactions with pyrazolones. The amino-bis-pyrazolone products are obtained in excellent yields and stereoselectivities by employing a very low loading of 1 mol % of a bifunctional squaramide organocatalyst. Depending on the substitution at position 4 of the pyrazolones, the new protocol allows for the generation of one or two tetrasubstituted stereocenters, including a one-pot version combing the Mannich reaction with a base-mediated halogenation.
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American Chemical SocietyISSN Search the Publication Forum
0022-3263Publication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/27022663
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