An amine protecting group deprotectable under nearly neutral oxidative conditions

Autor: Shahien Shahsavari, Chase McNamara, Mark Sylvester, Emily Bromley, Savannah Joslin, Bao-Yuan Lu, Shiyue Fang
Jazyk: angličtina
Rok vydání: 2018
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 1750-1757 (2018)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.14.149
Popis: The 1,3-dithiane-based dM-Dmoc group was studied for the protection of amino groups. Protection was achieved under mild conditions for aliphatic amines, and under highly reactive conditions for the less reactive arylamines. Moderate to excellent yields were obtained. Deprotection was performed by oxidation followed by treating with a weak base. The yields were good to excellent. The new amino protecting group offers a different dimension of orthogonality in reference to the commonly used amino protecting groups in terms of deprotection conditions. It is expected to allow a collection of transformations to be carried out on the protected substrates that are unattainable using any known protecting groups.
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