A metal-free BF3·OEt2 mediated chemoselective protocol for the synthesis of propargylic cyclic imines

A chemoselective and metal/additive-free protocol for the synthesis of propargylic cyclic imine derivatives via (3 + 2)-cycloaddition of donor–acceptor cyclopropanes and alkynylnitriles in the presence of BF3·OEt2 has been established. The newly developed methodology provided access to a variety of...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-01, Vol.20 (24), p.4933-4941
Main Authors: Singh, Prasoon Raj, Gopal, Braj, Kumar, Madan, Goswami, Avijit
Format: Article
Language:English
Subjects:
Amines
Cycloaddition
Cyclopropane
Imines
Organic compounds
Synthesis
Online Access:Get full text
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Summary:A chemoselective and metal/additive-free protocol for the synthesis of propargylic cyclic imine derivatives via (3 + 2)-cycloaddition of donor–acceptor cyclopropanes and alkynylnitriles in the presence of BF3·OEt2 has been established. The newly developed methodology provided access to a variety of propargylic cyclic imines in good to excellent yields. In addition, the synthesis of propargylic amines and the corresponding very stable enol derivatives from the title compound is also explored.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00530a