Journal
ACS CATALYSIS
Volume 11, Issue 20, Pages 12729-12735Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c03635
Keywords
asymmetric hydrogenation; DuanPhos; alpha-iminoketones; vicinal amino alcohols; stepwise transformation
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Funding
- Science, Technology and Innovation Commission of Shenzhen [JCYJ20190809160211372]
- National Natural Science Foundation of China [21991113]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Shenzhen Clean Energy Research Institute [CERI-KY-2019003]
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This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-iminoketones for accessing chiral vicinal amino alcohols. The methodology offers advantages such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields and stereoselectivities. Furthermore, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.
This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.
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