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.

General synthesis of unnatural 4-, 5-, 6-, and 7-bromo-d-tryptophans by means of a regioselective indole alkylation

Bartoccini, Francesca
Writing – Original Draft Preparation
;
Fanini, Fabiola
Investigation
;
Retini, Michele
Membro del Collaboration Group
;
Piersanti, Giovanni
2020

Abstract

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11576/2676899
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