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Issue 4, 2018
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Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems

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Abstract

Cyclic enamines are important synthons for many synthetic and pharmacological targets. Here, we report an inexpensive, catalyst-free, multigram-scale synthesis for cyclic enamines with exocyclic double bonds and four- to seven-membered rings. This strategy is more conducive to scale up, permissive of functionalization around the cyclic system, and less sensitive to the nature of the N-protecting group than previously-described methods for cyclic enamine synthesis. Further, we explore application of these enamines to the synthesis of highly-strained spirocyclic 3N-cyclopropyl scaffolds.

Graphical abstract: Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems

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Supplementary files

Article information


Submitted
30 Oct 2017
Accepted
21 Dec 2017
First published
21 Dec 2017

Org. Biomol. Chem., 2018,16, 652-656
Article type
Paper

Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems

P. Kumar, O. Zainul and S. T. Laughlin, Org. Biomol. Chem., 2018, 16, 652
DOI: 10.1039/C7OB02659E

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