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Synthesis 2009(5): 824-828  
DOI: 10.1055/s-0028-1083333
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Clean, Facile, and Stereospecific Synthesis of α-Oxoketene O,S-Acetals in Water

Yan Li, Qian Zhang*, Xin Cheng, Qun Liu*, Xiaohong Xu
Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. of China
e-Mail: zhangq651@nenu.edu.cn;
Further Information

Publication History

Received 25 September 2008
Publication Date:
27 January 2009 (online)

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Abstract

A facile and practical method for the stereospecific synthesis of α-oxoketene O,S-acetals in water has been developed. Catalyzed by tetrabutylammonium bromide at room temperature, the one-pot reaction of various β-dicarbonyl compounds, 2-bromoethanol, and carbon disulfide, in the presence of potassium carbonate, leads to the corresponding α-oxoketene O,S-acetals stereospecifically in good to excellent yields. The catalyst in the aqueous phase can be recycled after the separation of the organic products.

Key words

α-oxoketene O,S-acetals - one-pot synthesis - stereo­specificity - tetrabutylammonium bromide - water

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14

Crystal data for 3d: C14H15NO4S, white needle crystals, M = 293.33, monoclinic, C2/c, a = 15.640(5) Å, b = 8.249(5) Å, c = 23.035(5) Å, α = 90.000(5)˚, β = 106.460(5)˚, γ = 90.000(5)˚, V = 2850(2) ų, Z = 8, T = 293(2) K, F 000 = 1232, R 1 = 0.0490, ωR 2 = 0.1237. The CCDC deposition number 661621.