Journal
ORGANIC LETTERS
Volume 23, Issue 23, Pages 9112-9117Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03430
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Funding
- National Natural Science Foundation of China [21690074]
- Chinese Academy of Sciences [DICP I202002]
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A biomimetic asymmetric reduction method for 2-functionalized quinolines using the chiral and regenerable NAD(P)H model CYNAM has been successfully developed, providing chiral 2-functionalized tetrahydroquinolines with up to 99% ee. By utilizing this method as a key step, a chiral and potent opioid analgesic containing a 1,2,3,4-tetrahydroquinoline motif was synthesized with high overall yield.
Biomimetic asymmetric reduction of 2-functionalized quinolines has been successfully developed with the chiral and regenerable NAD(P)H model CYNAM in the presence of transfer catalyst simple achiral phosphoric acids, providing the chiral 2-functionalized tetrahydroquinolines with up to 99% ee. Using this methodology as a key step, a chiral and potent opioid analgesic containing a 1,2,3,4-tetrahydroquinoline motif was synthesized with high overall yield.
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