Campus Units

Center for Biorenewable Chemicals, Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

2-5-2014

Journal or Book Title

Organic Letters

Volume

16

Issue

4

First Page

1124

Last Page

1127

DOI

10.1021/ol403733n

Abstract

The first successful inverse electron-demand Diels–Alder has been demonstrated with the 2-pyrone methyl coumalate in conjunction with substituted indoles. Utilizing 1-alkyl-3-chloroindoles as the electron-rich dienophile efficiently generates carbazoles without the need for additional metal catalysts. Through a thermal, one-pot Diels–Alder/decarboxylation/elimination domino sequence, access to a class of 3-methylcarbazoles is rapidly generated with exclusive regiocontrol in up to 90% yield.

Comments

Reprinted (adapted) with permission from Organic Letters, 16(4); 1124-1127. Doi: 10.1021/ol403733n. Copyright 2014 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

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