Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts

Dan Li, Yuling Yang, Minmin Zhang, Linqing Wang, Yingfan Xu, Dongxu Yang () and Rui Wang ()
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Dan Li: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University
Yuling Yang: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University
Minmin Zhang: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University
Linqing Wang: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University
Yingfan Xu: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University
Dongxu Yang: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University
Rui Wang: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Institute of Drug Design & Synthesis, School of Basic Medical Sciences, Lanzhou University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Kinetic resolution (KR) of racemic starting materials is a powerful and practical alternative to prepare valuable enantiomerically enriched compounds. A magnesium-catalyzed kinetic resolution based on a designed intramolecular vinylogous Michael reaction is disclosed. Here we show a synergistic catalytic strategy based on the development of chiral ligands. Substrates containing linear allylic ester structures are designed and synthesized to construct key [6.6.5]-tricyclic chiral skeletons via this kinetic resolution process. Detailed mechanistic studies reveal a rational mechanism for the current intramolecular vinylogous KR reaction. The desired direct intramolecular asymmetric vinylogous Michael reaction of linear allylic esters is realized in high efficiency and enantioselectivity with the synergistic catalytic system.

Date: 2020
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DOI: 10.1038/s41467-020-16486-0

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