Synthesis 2022; 54(22): 5089-5098
DOI: 10.1055/s-0040-1719894
paper

Convenient Approach to Bicyclic Sultams

Sergiy L. Filimonchuk
a   Department of Organophosphorus Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02660, Ukraine
,
Kostiantyn Nazarenko
a   Department of Organophosphorus Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02660, Ukraine
b   Enamine Ltd, Oleksandra Matrosova Street 23, Kyiv, 01103, Ukraine
,
Tetiana Shvydenko
a   Department of Organophosphorus Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02660, Ukraine
,
Kostiantyn Shvydenko
a   Department of Organophosphorus Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02660, Ukraine
,
Eduard B. Rusanov
a   Department of Organophosphorus Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02660, Ukraine
,
a   Department of Organophosphorus Chemistry, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kyiv-94, 02660, Ukraine
› Author Affiliations


Abstract

A method for the synthesis of aminomethyl-substituted five-membered sultams has been developed. The aminomethyl sultams were synthesized from the corresponding iodomethyl derivatives by nucleophilic substitution of the iodine atom with sodium azide followed by reduction on Pd/C. This method was further expanded to side-chain-substituted sultams, starting from amino acid esters, to obtain aminomethyl-containing bicycles. The simple practical procedure and available starting amino acid esters, including chiral examples, make various bicyclic sultams readily available.

Supporting Information



Publication History

Received: 03 December 2021

Accepted after revision: 22 December 2021

Article published online:
15 February 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany