Azide-free synthesis of Boc-protected (3R, 4S)-3, 4-dihydroxypiperidine. (11th May 2022)

• Record Type: Journal Article
• Authors: Fezzardi, Paola; Fabbrini, Danilo; Relitti, Nicola; Ferrigno, Federica; Rossetti, Ilaria; Sferrazza, Alessio; Petrocchi, Alessia; Montalbetti, Christian
• Is Part Of: Tetrahedron letters. Volume 97(2022)
• Publication Date: 2022-05-11
• Subjects: Azide-free -- 2-deoxy-d-ribose -- Chiral diol -- (3R, 4S)-3, 4-dihydroxypiperidine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.153789
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Boc-protected (3 R, 4 S )-3, 4-dihydroxypiperidine diol 1 is an enantiomerically pure, highly valuable synthetic intermediate. Herein we report the development of two scalable synthetic strategies avoiding the use of hazardous sodium azide, as well as the formation of azido intermediates. Starting from the readily available 2-deoxy-d -ribose, it was possible to produce a substantial amount of diol 1 following two distinct routes, without a significant decrease in performance when scaling up from 1- to 230-mmol.