Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles

文献情報

出版日 2016-10-19

DOI 10.1039/C6QO00446F

インパクトファクター 5.281

著者

Zi-Qi Zhu, Lei Yin, Yang Wang, Yang Shen, Can Li, Guang-Jian Mei, Feng Shi

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要旨

A catalytic asymmetric [3 + 2] cyclodimerization of 3-alkyl-2-vinylindoles has been established, which efficiently constructed a pyrrolo[1,2-a]indole scaffold with three contiguous stereogenic centers in a diastereo- and enantioselective fashion (up to 98% yield, >95 : 5 dr, 98 : 2 er). This reaction not only represents the first catalytic asymmetric version of this type of [3 + 2] cyclodimerization, but also supplies important examples for using 2-vinylindoles as nitrogen–carbon–carbon (NCC) building blocks in asymmetric catalysis and synthesis. More importantly, this reaction also provides an efficient method for enantioselectively constructing biologically significant pyrrolo[1,2-a]indole scaffolds.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles

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