Organic & Biomolecular Chemistry 2011-06-21

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

Naoto Kojima, Shogo Nishijima, Kaoru Tsuge, Tetsuaki Tanaka

Index: Org. Biomol. Chem. 9(12) , 4425-8, (2011)

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Abstract

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%.