One-Pot Preparation of Tricyclo[5.2.2.04,9]undecanes via Cu-Catalyzed Asymmetric Carboboration of Cyclohexadienone-Tethered Allenes
| Autor: | Guo-Qiang Lin, Wen-Bo Ye, Kai-Rui Feng, Zhi-Tao He, Ping Tian, Yun-Xuan Tan, Yi-Fan Wang |
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| Rok vydání: | 2020 |
| Předmět: |
Tandem
010405 organic chemistry Chemistry Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Borylation 0104 chemical sciences Catalysis Kinetic resolution Aldol reaction Intramolecular force Physical and Theoretical Chemistry Conjugate |
| Zdroj: | Organic Letters. 23:607-611 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.0c04191 |
| Popis: | The Cu-catalyzed asymmetric carboboration of cyclohexadienone-tethered allenes has been achieved through regioselective β-borylation of the allenes and subsequent conjugate addition to cyclohexadienones, affording cis-bicyclic frameworks with acceptable yields and high to excellent enantioselectivities. Further conjugate borylation of the carboboration products proved to be a favorable kinetic resolution process, which improved the overall enantioselectivity. Finally, one-pot preparation of highly enantioenriched tricyclo[5.2.2.04,9]undecanes was developed from the cyclohexadienone-tethered allenes through β-borylation/1,4-addition and subsequent tandem oxidation/intramolecular aldol reaction. |
| Databáze: | OpenAIRE |
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