Organic Letters
Organic Letters
5 years ago

Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization

Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization
Shao-Li Xu, Feng Shi, Guo-Hao Li, Guang-Jian Mei, Chen-Yu Bian, Wen-Qin Zheng
The first catalytic asymmetric construction of the tryptanthrin skeleton has been established, taking advantage of a palladium(0)/chiral ligand-catalyzed enantioselective decarboxylative [4 + 2] cyclization of vinyl benzoxazinanones with isatins. This reaction has not only provided a direct and efficient method for constructing chiral tryptanthrin skeleta in high yields and excellent enantioselectivities (up to 97% yield, >99% ee) but also represents the first catalytic asymmetric decarboxylative cyclization of vinyl benzoxazinanones with isatins.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01336

DOI: 10.1021/acs.orglett.7b01336

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