Catalytic Chiral Leaving Group Strategy for Asymmetric Substitutions at sp3-Hybridized Carbon Atoms : Kinetic Resolution of β-Amino Alcohols by p-Methoxybenzylation
Kuroda, Yusuke Kyoto University
Harada, Shingo Kyoto University
Oonishi, Akinori Kyoto University
Kiyama, Hiroki Kyoto University
Yamaoka, Yousuke Kyoto University
Yamada, Ken-ichi Kyoto University|Tokushima University Tokushima University Educator and Researcher Directory
Takasu, Kiyosei Kyoto University
Brønsted acid catalysis
We developed a catalytic strategy for asymmetric substitution reactions at sp3-hybridized carbon atoms using a chiral alkylating agent generated in situ from trichloroacetimidate and a chiral phosphoric acid. The resulting chiral p-methoxybenzyl phosphate selectively reacted with β-amino alcohols rather than those without the β-NH functionality. An electronically and sterically tuned chiral phosphoric acid was developed to enable the kinetic resolution of amino alcohols, with good enantioselectivity, through p-methoxybenzylation.
Angewandte Chemie International Edition
WILEY-VCH Verlag GmbH & Co. KGaA
This is the peer-reviewed version of the following article: Y. Kuroda, S. Harada, A. Oonishi, H. Kiyama, Y. Yamaoka, K.-i. Yamada, K. Takasu, Angew. Chem. Int. Ed. 2016, 55, 13137, which has been published in final form at https://doi.org/10.1002/anie.201607208. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving.
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