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

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 effi...

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Bibliographic Details
Published in:Organic letters 2017-06, Vol.19 (12), p.3219-3222
Main Authors: Mei, Guang-Jian, Bian, Chen-Yu, Li, Guo-Hao, Xu, Shao-Li, Zheng, Wen-Qin, Shi, Feng
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01336