Enantioselective Synthesis of Tryptophan Derivatives by a Tandem Friedel–Crafts Conjugate Addition/Asymmetric Protonation Reaction
Journal of the American Chemical SocietyPublished 5 March 2012
Madeleine E. Kieffer, Lindsay M. Repka, Sarah E. Reisman
Citations121
SJR quartileQ1
SJR score5.55
SNIP2.61
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TL;DR
The tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported, and is the first example of a tandem conjugates addition-to-protonation Reaction using a BINOL·SnCl(4) complex as the catalyst.
Abstract
The tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3'-dibromo-BINOL in the presence of stoichiometric SnCl(4), and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOL·SnCl(4) complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.
Keywords
Chemistry
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