Diastereo- and enantioselective construction of biologically important pyrrolo[1,2-a]indole scaffolds via catalytic asymmetric [3 + 2] cyclodimerizations of 3-alkyl-2-vinylindoles
Literature Information
Publication Date
2016-10-19
DOI
10.1039/C6QO00446F
Impact Factor
5.281
Authors
Zi-Qi Zhu, Lei Yin, Yang Wang, Yang Shen, Can Li, Guang-Jian Mei, Feng Shi
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
2-Methyl-2-propanyl (1-cyclobutyl-3-hydroxy-2-propanyl)carbamate
CAS Number:
816429-99-9
Molecular Formula:
C12H23NO3
![3-(benzotriazol-1-yl)-N-[[2-[(3-bromophenyl)methoxy]phenyl]methylideneamino]propanamide structure](https://static.chemtradehub.com/structs/559/5595-78-8-0a32.webp "3-(benzotriazol-1-yl)-N-[[2-[(3-bromophenyl)methoxy]phenyl]methylideneamino]propanamide structure")
3-(benzotriazol-1-yl)-N-[[2-[(3-bromophenyl)methoxy]phenyl]methylideneamino]propanamide
CAS Number:
5595-78-8
Molecular Formula:
C32H52O2
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