Journal
ORGANIC LETTERS
Volume 23, Issue 13, Pages 5153-5157Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01689
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Funding
- National Natural Science Foundation of China [21532003, 21871152, 21790332]
- 111 project of the Ministry of Education of China [B06005]
- Frontiers Sciences Center for New Organic Matter (Nankai University) [63181206]
- Fundamental Research Funds for the Central Universities (Nankai University) [020-63191746]
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An efficient asymmetric hydrogenation method using a chiral spiro iridium catalyst has been developed to convert racemic gamma-substituted cyclic beta-ketoesters into chiral cyclic beta-hydroxy esters with three stereocenters. The reaction provides high yields (84-97%) with good to excellent enantioselectivities (69->99% ee) and cis,cis-selectivities (up to >99:1).
An efficient asymmetric hydrogenation of racemic gamma-substituted cyclic beta-ketoesters via dynamic kinetic resolution to provide chiral cyclic beta-hydroxy esters with three contiguous stereocenters is reported. Using a chiral spiro iridium catalyst (R)-S (Ir-SpiroSAP), a series of racemic gamma-aryl/alkyl substituted cyclic P-ketoesters were hydrogenated to the corresponding chiral cyclic beta-hydroxy esters in high yields (84-97%) with good to excellent enantioselectivities (69->99% ee) and cis,cis-selectivities (up to >99:1).
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