Issue 18, 2018

Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation

Abstract

A new type of 2,4-dienal with α-substitutions and featuring a benzofulvene skeleton has been designed and utilised in asymmetric Diels–Alder cycloaddition reactions with 3-olefinic oxindoles under the trienamine catalysis of a chiral secondary amine. An array of chiral polyhydrofluorene frameworks with complex molecular structures are constructed efficiently, generally in fair to high yields with good diastereoselectivity and excellent enantioselectivity.

Graphical abstract: Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation

Supplementary files

Article information

Article type
Research Article
Submitted
02 jul 2018
Accepted
07 ago 2018
First published
08 ago 2018

Org. Chem. Front., 2018,5, 2676-2679

Asymmetric Diels–Alder cycloadditions of benzofulvene-based 2,4-dienals via trienamine activation

J. Yue, G. Ran, X. Yang, W. Du and Y. Chen, Org. Chem. Front., 2018, 5, 2676 DOI: 10.1039/C8QO00653A

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