Journal
SYNTHESIS-STUTTGART
Volume -, Issue 13, Pages 2198-2204Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2005-869978
Keywords
Friedel-Crafts reaction; indolyl glycine; indole derivative; glyoxylate imine; spontaneous reaction
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Mannich-type Friedel-Crafts reaction between indoles and ethyl glyoxylate imines proceeded spontaneously in the absence of an acid catalyst. Ethyl alpha-(3-indolyl)glycinates were obtained in moderate to high yields. Reaction with (R)-alpha-methylbenzylamine derived imine afforded chiral alpha-(3-indolyl)glycinates with good diastereoselectivities (up to 96:4).
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