期刊
ORGANIC LETTERS
卷 23, 期 16, 页码 6299-6304出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02093
关键词
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资金
- Shanghai Institute of Materia Medica
- Chinese Academy of Sciences
- National Natural Science Foundation of China [21772211, 21920102003]
- Youth Innovation Promotion Association CAS [2014229, 2018293]
- Institutes for Drug Discovery and Development, Chinese Academy of Sciences [CASIMM0120163006]
- Science and Technology Commission of Shanghai Municipality [17JC1405000, 21ZR1475400, 18431907100]
- Program of Shanghai Academic Research Leader [19XD1424600]
- National Science AMP
- Technology Major Project Key New Drug Creation and Manufacturing Program, China [2018ZX09711002-006]
In this study, the palladium-catalyzed asymmetric acyl-carbamoylation reaction was reported, producing alpha-quaternary chiral cycloketone with high yields and excellent enantioselectivity. The reaction proceeded via asymmetric 1,2-migratory insertions of acyl-Pd into alkenes and subsequent migratory insertion of isocyanides into C(sp(3))-Pd-II. The product could be further diversified, showcasing the synthetic utility of this protocol.
Herein, we report the palladium-catalyzed asymmetric acyl-carbamoylation of an alkene by employing thioesters as the acyl electrophiles and t-BuNC as the carbamoyl reagent, affording an alpha-quaternary chiral cycloketone in synthetically useful yields with excellent enantioselectivity. The reaction proceeded via asymmetric 1,2-migratory insertions of acyl-Pd into alkenes and subsequent migratory insertion of isocyanides into C(sp(3))-Pd-II. The product could be diversified to some valuable skeletons with retention of enantiopurity, demonstrating the synthetic utility of this protocol.
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