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An Efficient Synthetic Method to Nonnatural α- and β-Tryptophan Analogues via Friedel-Crafts Alkylation of Indoles with Nitroacrylates

✍ Scribed by Yong Sui; Li Liu; Dong Wang; Yong-Jun Chen

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 123 KB
Volume: 25
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.200790190

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✦ Synopsis

Abstract

The Friedel‐Crafts alkylation of indoles with nitroacrylates could provide α‐ and β‐tryptophan nitro‐precursors, respectively, in moderate to good yields under Lewis acid catalysis. The diastereoselectivities of the reaction were enhanced by using 2‐substituted indoles. The alkylation products could be easily transformed to nonnatural tryptophan derivatives.

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