Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters Catalyzed by Chiral Oxazaborolidinium Ion: Total Synthesis of (+)-Hamavellone B
| Autor: | Jae Yeon Kim, Do Hyun Ryu, Su Yong Shim, Geum-Sook Hwang, Miso Nam |
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| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Cyclopropanes Molecular Structure 010405 organic chemistry Cyclopropanation Stereochemistry Organic Chemistry Enantioselective synthesis Absolute configuration Molecular Conformation Total synthesis Stereoisomerism 010402 general chemistry Crystallography X-Ray 01 natural sciences Biochemistry Catalysis 0104 chemical sciences Cyclopropane Stereocenter chemistry.chemical_compound chemistry Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Organic letters. 18(2) |
| ISSN: | 1523-7052 |
| Popis: | Chiral oxazaborolidinium ion-catalyzed asymmetric cyclopropanation of α- or α,β-substituted acroleins with α-alkyl-α-diazoesters has been developed. With this methodology, chiral functionalized cyclopropanes containing a quaternary stereogenic center were obtained with high to excellent enantioselectivities (up to >99% ee). The synthetic utility of optically enriched functionalized cyclopropane was demonstrated in the first total synthesis of (+)-hamavellone B, which establishes the absolute configuration of natural (+)-hamavellone B. |
| Databáze: | OpenAIRE |
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