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Organocatalytic Enantioselective [8+4] Cycloadditions of Isobenzofulvenes for the Construction of Bicyclo[4.2.1]nonanes

Organocatalytic Enantioselective [8+4] Cycloadditions of Isobenzofulvenes for the Construction of... The [8+4] cycloaddition of indene‐2‐carbaldehydes with indole‐2,3‐quinodimethanes and pyrrolidone‐3,4‐dienes is described, affording indole and pyrrolidone annulated bicyclo[4.2.1]nonanes in a highly peri‐, diastereo‐, and enantioselective fashion in the presence of a secondary amine catalyst. This reaction, which proceeds through catalytically generated isobenzofulvenes, represents the first asymmetric version of high‐order [8+4] cycloaddition. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

Organocatalytic Enantioselective [8+4] Cycloadditions of Isobenzofulvenes for the Construction of Bicyclo[4.2.1]nonanes

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References (8)

Publisher
Wiley
Copyright
© 2021 SIOC, CAS, Shanghai & WILEY‐VCH GmbH
ISSN
1001-604X
eISSN
1614-7065
DOI
10.1002/cjoc.202100250
Publisher site
See Article on Publisher Site

Abstract

The [8+4] cycloaddition of indene‐2‐carbaldehydes with indole‐2,3‐quinodimethanes and pyrrolidone‐3,4‐dienes is described, affording indole and pyrrolidone annulated bicyclo[4.2.1]nonanes in a highly peri‐, diastereo‐, and enantioselective fashion in the presence of a secondary amine catalyst. This reaction, which proceeds through catalytically generated isobenzofulvenes, represents the first asymmetric version of high‐order [8+4] cycloaddition.

Journal

Chinese Journal of ChemistryWiley

Published: Dec 1, 2021

Keywords: Organocatalysis; Isobenzofulvene; Electron‐deficient dienes; Cycloaddition; Enantioselectivity

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