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Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives.

Organic & biomolecular chemistry (2011-05-10)
Naoto Kojima, Shogo Nishijima, Kaoru Tsuge, Tetsuaki Tanaka
ABSTRAKT

The asymmetric alkynylation of aliphatic and aromatic aldehydes with propiolates was mediated by dialkylzinc and a novel prolinol catalyst without high reagent loading and any additives, such as Ti(Oi-Pr)(4), to give the corresponding γ-hydroxy-α,β-acetylenic esters with high enantiomeric excess of up to 95%.

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Sigma-Aldrich
(S)-(+)-2-Pyrrolidinemethanol, 97%
Sigma-Aldrich
Propiolic acid, 95%