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Organocatalyst-mediated five-pot synthesis of (–)-quinine
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Organocatalyst-mediated five-pot synthesis of (–)-quinine
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Journal Article
Organocatalyst-mediated five-pot synthesis of (–)-quinine
2022
Overview
In this work, the enantioselective total synthesis of (–)-quinine has been accomplished in a pot-economical manner using five reaction vessels. In the first pot, reactions involve the diphenylprolinol silyl ether-mediated Michael reaction, aza-Henry reaction, hemiaminalization, and elimination of HNO
2
(five reactions), affording a chiral tetrahydropyridine with excellent enantioselectivity. In the second pot, five reactions proceed with excellent diastereoselectivity to afford a trisubstituted piperidine with the desired stereochemistry. A further five reactions are carried out in the last one-pot sequence.
Syntheses of quinine have fascinated organic chemists for over a hundred years. Here, the authors developed an organocatalyst-mediated pot-economical enantioselective total synthesis using five reaction vessels.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
