Application of pyrrolo-protected amino aldehydes in the stereoselective synthesis of anti 1,2-amino alcohols.

Sauer M, Beemelmanns C (2022) Application of pyrrolo-protected amino aldehydes in the stereoselective synthesis of anti 1,2-amino alcohols. ChemCom 58(64), 8990-8993.

Abstract

Here, we demonstrate the applicability of the 2,5-dimethylpyrrolo unit as a complementary N-protecting group in the highly diastereoselective synthesis of more than 20 different anti-amino alcohols (63-90% yield with up to 20:1 dr). Cleavage of the pyrrolo-N-protecting group was accomplished e.g. in the presence of NH2OH under microwave conditions with yields exceeding 80%. The applicability of the protecting groups was further demostrated by the shortest yet reported total synthesis of the sphinganine-like natural product clavaminol A. The application of the N-pyrrolo protecting group also offers the possibility analyse product micxtures by NMR measurements due to the absence of conformational isomers, which are otherwise common for N-protecting groups.

Leibniz-HKI-Autor*innen

Christine Beemelmanns
Maria Sauer

Identifier

doi: 10.1039/D2CC02317B

PMID: 35861502