Cu(ii )/SPDO complex catalyzed asymmetric Baeyer–Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6
| Autor: | Chang-Sheng Zhang, Ya-Ping Shao, Fu-Min Zhang, Xue Han, Xiao-Ming Zhang, Kun Zhang, Yong-Qiang Tu |
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| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Chemical Science. 13:8429-8435 |
| ISSN: | 2041-6539 2041-6520 |
| DOI: | 10.1039/d2sc02079c |
| Popis: | A novel classical kinetic resolution of 2-aryl-substituted or 2,3-disubstituted cyclobutanones of Baeyer-Villiger oxidation catalyzed by a Cu(ii)/SPDO complex is reported for the first time, producing normal lactones in excellent enantioselectivities (up to 96% ee) and regioselectivities (up to20/1), along with unreacted ketones in excellent enantioselectivities (up to 99% ee). The current transformation features a wide substrate scope. Moreover, catalytic asymmetric total syntheses of natural eupomatilones 5 and 6 are achieved in nine steps from commercially available 3-methylcyclobutan-1-one. |
| Databáze: | OpenAIRE |
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