Practical Enantioselective Reduction of Ketones Using Oxazaborolidine Catalysts Generated In Situ from Chiral Lactam Alcohols
| Autor: | Ryo C. Yanagita, Yasuhiro Kawanami |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
In situ
Lactams asymmetric synthesis Pharmaceutical Science reduction Review Borane 010402 general chemistry 01 natural sciences Catalysis Analytical Chemistry lcsh:QD241-441 Reduction (complexity) Heterocyclic Compounds 1-Ring chemistry.chemical_compound lcsh:Organic chemistry Drug Discovery Organic chemistry Physical and Theoretical Chemistry Boranes borane lactam alcohol Trifluoromethyl 010405 organic chemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Ketones 0104 chemical sciences chemistry Chemistry (miscellaneous) Alcohols Lactam Molecular Medicine enantioselective CBS catalyst Oxidation-Reduction |
| Zdroj: | Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry Molecules, Vol 23, Iss 10, p 2408 (2018) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules23102408 |
| Popis: | Oxazaborolidine catalyst (CBS catalyst) has been extensively used for catalytic borane reduction with a predictable absolute stereochemistry and high enantioselectivity. However, the use of isolated CBS catalyst sometimes has the drawback of low reproducibility due to the aging of the CBS catalyst during storage. Therefore, we investigated a more reliable and practical method for the reduction of a variety of ketones including challenging substrates, primary aliphatic ketones, α,β-enones, and trifluoromethyl ketones. This review surveys the developments in borane reduction using oxazaborolidine catalysts generated in situ from chiral lactam alcohols and borane. |
| Databáze: | OpenAIRE |
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