Double Addition of Propargylzinc Reagents to Acylcyanohydrins and Cyanocarbonates

An efficient and mild synthetic methodology of double addition of propargylzinc reagents onto acylcyanohydrins and cyanocarbonates has been developed. After optimization of reaction conditions, dipropargylic α,α‐disubstituted hydroxyamides and N‐Boc‐protected amino alcohols have been straightforward...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-10, Vol.2022 (40), p.n/a
Main Authors: Liu, Meng, Dwadnia, Nejib, Chevalier, Tony, Hemon‐Ribaud, Annie, Pearson‐Long, Morwenna S. M., Boeda, Fabien, Bertus, Philippe
Format: Article
Language:English
Subjects:
[2+2+2] Cycloaddition
Alcohols
Chemical reactions
Cobalt compounds
Cycloaddition
Double addition
Nitrile
Optimization
Organozinc reagent
Propargylation
Pyridine
Reagents
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Summary:An efficient and mild synthetic methodology of double addition of propargylzinc reagents onto acylcyanohydrins and cyanocarbonates has been developed. After optimization of reaction conditions, dipropargylic α,α‐disubstituted hydroxyamides and N‐Boc‐protected amino alcohols have been straightforwardly prepared in good yields. The valorization of the so‐obtained compounds was undertaken by cobalt‐catalyzed [2+2+2] cycloaddition reactions to provide functionalized pyridine derivatives. Two darts in the middle! This work reports the double addition of propargylzinc reagents to nitriles (acylcyanohydrins and cyanocarbonates). This methodology provides a straightforward access to dipropargylic α,α‐disubstituted hydroxyamides or N‐Boc‐protected amino alcohols which can be converted into functionalized pyridine derivatives after cobalt‐catalyzed [2+2+2] cycloaddition reactions involving nitriles.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200891