Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols
Open Access
- 15 November 2016
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 8 (3) , 1811-1814
- https://doi.org/10.1039/c6sc04609f
Abstract
We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80–95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.Keywords
Funding Information
- National Natural Science Foundation of China
- Ministry of Education of the People's Republic of China (B06005)
This publication has 34 references indexed in Scilit:
- Replacing Phosphorus with Sulfur for the Efficient Hydrogenation of EstersAngewandte Chemie International Edition in English, 2013
- From Esters to Alcohols and Back with Ruthenium and Osmium CatalystsAngewandte Chemie International Edition in English, 2012
- Catalytic Hydrogenation of Carboxamides and Esters by Well-Defined Cp*Ru Complexes Bearing a Protic Amine LigandJournal of the American Chemical Society, 2011
- Asymmetric Synthesis of Chiral N-Sulfinyl 3-Alkyl- and 3-Arylpiperidines by α-Alkylation of N-Sulfinyl Imidates with 1-Chloro-3-iodopropaneThe Journal of Organic Chemistry, 2010
- Stereocontrol in Radical Cyclization: Change in Rate-Determining StepOrganic Letters, 2010
- A [3 + 3] Annelation Approach to (+)-Rhopaloic Acid BOrganic Letters, 2007
- Catalytic hydrogenation of polar organic functionalities based on Ru-mediated heterolytic dihydrogen cleavageChemical Communications, 2007
- Catalytic asymmetric hydrogenation of aldehydesChemical Communications, 2007
- A Stereocontrolled Synthesis of (+)- Rhopaloic Acid A Using a Dioxabicyclo- [3.2.1]octane Chiral Building BlockHETEROCYCLES, 2003
- N-n-Propyl-Substituted 3-(Dimethylphenyl)piperidines Display Novel Discriminative Properties between Dopamine Receptor Subtypes: Synthesis and Receptor Binding StudiesJournal of Medicinal Chemistry, 1998