Transition metal-free generation of N-unsubstituted imines from benzyl azides: synthesis of N-unsubstituted homoallylic amines

The Journal of Organic Chemistry
Suman PramanikPrasanta Ghorai

Abstract

An efficient transition metal-free approach for the generation of N-unsubstituted imines from azides followed by trapping with allyl nucleophile to provide N-unsubstituted homoallylic amines has been described. Although catalytic KO(t)Bu in DMSO is sufficient to allow imine generation, stoichiometric KO(t)Bu is essential in THF. Further, an enantio- and diastereoselective synthesis of homoallylic amines from benzyl azide has also been exemplified.

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Citations

Dec 10, 2016·Chemical Communications : Chem Comm·Marco BortoluzziStefano Zacchini
Feb 13, 2019·Organic & Biomolecular Chemistry·Nikhil R TaskerPeter Wipf
Apr 11, 2019·Organic & Biomolecular Chemistry·Angela S Carlson, Joseph J Topczewski
Dec 20, 2019·Organic Letters·Yuta KondoTakashi Ohshima
Nov 6, 2020·The Journal of Organic Chemistry·Luis M Mori-QuirozMichael D Clift
Nov 10, 2021·The Journal of Organic Chemistry·Hwi Yul JoJaiwook Park

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