Journal
ORGANIC LETTERS
Volume 23, Issue 18, Pages 7166-7170Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02568
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Funding
- National Natural Science Foundation of China [21690074, 21532006]
- Chinese Academy of Sciences [XDB17020300]
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The asymmetric reduction of tetrasubstituted olefins has seen significant development, leading to an urgent demand for an effective method. By mimicking the coenzyme NAD(P)H, researchers have successfully reduced 2,3-substituted 1H-inden-1-ones using the catalytic chiral NAD(P)H model CYNAM, achieving high yields (up to 98%) and good enantioselectivity (up to 99% ee). The reduced product can also be efficiently used for the concise synthesis of chiral bioactive molecules.
Because of the formidable development of the asymmetric reduction of tetrasubstituted olefins, an effective method is in urgent demand. Herein, through the biomimetic protocol of the coenzyme NAD(P)H, the reduction of tetrasubstituted olefin 2,3-substituted 1H-inden-1-ones has been successfully realized with the catalytic chiral NAD(P)H model CYNAM, which is hard to bring about via the common rhodium or iridium-based catalytic system, producing the corresponding products in good yield (up to 98%) with good enantioselectivity (up to 99% ee). Furthermore, the chiral bioactive molecule can be concisely synthesized from the reduced product.
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