Cu(ii)/SPDO complex catalyzed asymmetric Baeyer–Villiger oxidation of 2-arylcyclobutanones and its application for the total synthesis of eupomatilones 5 and 6 |
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| Authors: | Chang-Sheng Zhang Ya-Ping Shao Fu-Min Zhang Xue Han Xiao-Ming Zhang Kun Zhang Yong-Qiang Tu |
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| Institution: | State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000 P. R. China.; School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020 Guangdong P. R. China ; School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240 P. R. China |
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| Abstract: | 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 to >20/1), 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.A novel classical kinetic resolution of Baeyer–Villiger oxidation catalyzed by a Cu(ii)/SPDO complex with excellent enantioselectivity, regioselectivity and wide substrate scope is reported for the first time and explore the synthetic application. |
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