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Transition Metal-Free Generation of N-Unsubstituted Imines from Benzyl Azides: Synthesis of N-Unsubstituted Homoallylic Amines

Suman Pramanik, Reddy Rajasekhar Reddy and Prasanta Ghorai*

*Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Indore By-pass Road, Bhauri, Bhopal 462066, India, Email: pghoraiiiserb.ac.in

S. Pramanik, R. R. Reddy, P. Ghorai, J. Org. Chem., 2015, 80, 3656-3663.

DOI: 10.1021/jo502794q (free Supporting Information)


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Abstract

Stoichiometric KOtBu in THF enables an efficient transition metal-free approach for the generation of N-unsubstituted imines from azides. Trapping with allyl nucleophile provides N-unsubstituted homoallylic amines. Further, an enantio- and diastereoselective synthesis of homoallylic amines from benzyl azide has also been exemplified.

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Key Words

homoallylic amines


ID: J42-Y2015