Asymmetric Synthesis of beta(2)-Tryptophan Analogues via Friedel-Crafts Alkylation of Indoles with a Chiral Nitroacrylate

作者:Pavlov Nikola; Gilles Pierre; Didierjean Claude; Wenger Emmanuel; Naydenova Emilia; Martinez Jean; Calmes Monique*
来源:Journal of Organic Chemistry, 2011, 76(15): 6116-6124.
DOI:10.1021/jo200733t

摘要

The asymmetric Friedel-Crafts alkylation of various indoles with a chiral nitroacrylate provides optically active beta-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).

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