Journal
TETRAHEDRON LETTERS
Volume 61, Issue 22, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2020.151923
Keywords
Unnatural amino acid; Indole; Sulfamidate; Halotryptophans
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A general two-step approach to enantiopure bromotryptophans from unprotected bromoindoles has been developed. Indole nucleophiles prepared with MeMgCl in the presence of CuCl reacted with cyclic sulfamidates derived from enantiopure D-serine to form 4-, 5-, 6-, or 7-bromo-D-tryptophan and some other halogenated tryptophans in moderate yields but with complete regioselectivity. The bromotryptophan derivatives were deprotected using mild conditions. (C) 2020 Elsevier Ltd. All rights reserved.
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