Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 6, Pages 2477-2483Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c13273
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Funding
- Southern University of Science and Technology
- Shenzhen Science and Technology Innovation Committee [KQTD20150717103157174, JSGG20170821140353405]
- Key-Area Research and Development Program of Guangdong Province [2020B010188001]
- Innovative Team of Universities in Guangdong Province [2020KCXTD016]
- National Natural Science Foundation of China [21991113]
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A catalytic protocol for the enantio- and diastereoselective reduction of alpha-substituted-beta-keto carbonitriles is described, providing high yields of beta-hydroxy carbonitrile compounds with excellent selectivity. The methodology is suitable for rapid access to pharmaceutical intermediates Ipenoxazone and Tapentadol.
A catalytic protocol for the enantio- and diastereoselective reduction of alpha-substituted-beta-keto carbonitriles is described. The reaction involves a DKR-ATH process with the simultaneous construction of beta-hydroxy carbonitrile scaffolds with two contiguous stereogenic centers. A wide range of alpha-substituted-beta-keto carbonitriles were obtained in high yields (94%-98%) and excellent enantio- and diastereoselectivities (up to >99% ee, up to >99:1 dr). The origin of the diastereoselectivity was also rationalized by DFT calculations. Furthermore, this methodology offers rapid access to the pharmaceutical intermediates of Ipenoxazone and Tapentadol.
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