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DOI: 10.1055/s-0030-1261173
Me3Ga-Mediated Addition of Acetylenes to α-Keto Esters: A New Method for the Synthesis of α-Hydroxy Esters
Publication History
Publication Date:
10 August 2011 (online)
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Abstract
Trimethylgallium reagent was found to promote the addition of acetylenes to various α-keto esters. This reaction was efficiently carried out in anhydrous hexane at room temperature under mild conditions, and the corresponding α-hydroxy esters were obtained in good to excellent yields.
Key words
trimethylgallium - alkynylation - α-keto ester - α-hydroxy ester - acetylene
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
General Experimental
Procedure
In a 20 mL Schlenk reaction tube, 1 M solution
of Me3Ga (0.15 mL, 0.15 mmol, 1 M in toluene) and 4-methoxy-phenylacetylene
(20 mg, 0.15 mmol) were dissolved in anhyd hexane (1 mL) and stirred
for 1 h at r.t. under an nitrogen atmosphere. Then the mixture was
cooled to 0 ˚C and methyl benzoylformate (0.1 mmol) was
added, and stirred at r.t. for indicated time in Table
[²]
, then sat. NH4Cl
(1 mL) was added to quench the reaction. The aqueous layer was separated
and further extracted with EtOAc, the organic layers were combined
and dried. Evaporation of the solvent gave the crude product, which
was further purified by preparative TLC (PE-EtOAc = 10:1)
to give corresponding α-hydroxy esters.