Application of Dimedone Enamines as Protecting Groups for Amines and Peptides

A simple protocol for the protection of amines was realized through a base-catalyzed one-pot reaction of dimedone, β-nitroalkene, and amine. Employing this strategy, a variety of amines/amino acids were protected in excellent yields. These acid/base stable protected amines can be deprotected by eith...

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Bibliographic Details
Published in:Organic letters 2020-03, Vol.22 (6), p.2391-2395
Main Authors: Chithanna, Sivanna, Vyasamudri, Sameer, Yang, Ding-Yah
Format: Article
Language:English
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Summary:A simple protocol for the protection of amines was realized through a base-catalyzed one-pot reaction of dimedone, β-nitroalkene, and amine. Employing this strategy, a variety of amines/amino acids were protected in excellent yields. These acid/base stable protected amines can be deprotected by either ethylene diamine or hydrazine hydrate under mild conditions. The practical application of this orthogonal protecting group was demonstrated by the synthesis of cyclic peptide melanotan II via SPPS.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00586