Asymmetric synthesis of β2-tryptophan analogues via Friedel-Crafts alkylation of indoles with a chiral nitroacrylate

Nikola Pavlov; Pierre Gilles; Claude Didierjean; Emmanuel Wenger; Emilia Naydenova; Jean Martinez; Monique Calmès

doi:10.1021/jo200733t

Asymmetric synthesis of β2-tryptophan analogues via Friedel-Crafts alkylation of indoles with a chiral nitroacrylate

J Org Chem. 2011 Aug 5;76(15):6116-24. doi: 10.1021/jo200733t. Epub 2011 Jun 28.

Authors

Nikola Pavlov¹, Pierre Gilles, Claude Didierjean, Emmanuel Wenger, Emilia Naydenova, Jean Martinez, Monique Calmès

Affiliation

¹ Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS-Université Montpellier 1 et Université Montpellier 2, Bâtiment Chimie (17), Université Montpellier 2, place E. Bataillon, 34095 Montpellier cedex 5, France.

PMID: 21671594
DOI: 10.1021/jo200733t

Abstract

The asymmetric Friedel-Crafts alkylation of various indoles with a chiral nitroacrylate provides optically active β-tryptophan analogues after reduction of the nitro group and removal of the chiral auxiliary. This reaction generally occurs in good yield and high diastereoselectivity (up to 90:10).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acrylates / chemistry*
Alkylation
Indoles / chemistry*
Molecular Structure
Nitro Compounds / chemistry*
Stereoisomerism
Tryptophan / chemical synthesis*
Tryptophan / chemistry

Substances

Acrylates
Indoles
Nitro Compounds
Tryptophan