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Synthesis 2011(15): 2459-2465  
DOI: 10.1055/s-0030-1260096
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Functionalized Cyclopropane Derivatives via α-Thiocyanate Ketone-Based Three-Component Reaction

Fei-Yue Wu, Ying Li, Hui Feng, Qiong Wu, Bo Jiang*, Feng Shi, Shu-Jiang Tu*
School of Chemistry and Chemical Engineering, Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu, 221116, P. R. of China
Fax: +86(516)83500065; e-Mail: jiangchem@xznu.edu.cn; e-Mail: laotu@xznu.edu.cn;
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Publikationsverlauf

Received 30 March 2011
Publikationsdatum:
08. Juli 2011 (online)

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Abstract

α-Thiocyanate ketone-based three-component reactions have been established for the stereoselective synthesis of functionalized electron-deficient trans-cyclopropanes. The multicomponent reactions were conducted by reacting readily available and inexpensive starting materials under microwave irradiation. The procedures are very facile, highly stereoselective, and avoids the use of ylides.

Key words

multicomponent reactions - cyclopropanes - stereoselectivity - microwave heating

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15

Single-crystal growth was carried out in ethanol at room temperature. X-ray crystallographic analysis was performed with a Siemens SMART CCD and a Siemens P4 diffractometer (graphite monochromator, MoKα radiation λ = 0.71073 Å). Crystal data for 6a: Empirical formula: C18H11BrN2O; formula weight: 351.20; crystal dimensions 0.48 × 0.40 × 0.30 mm; triclinic; space group P1; a = 8.0590(10) Å, b = 10.3631(12) Å, c = 11.2581(13) Å, α = 63.9500(10)˚, β = 69.676(2)˚, γ = 67.348(2)˚; µ = 2.702 mm-¹; V = 761.34(16) ų; Z = 2; D(calcd) = 1.532 Mg/m³; F(000) = 352, S = 1.058, R 1 = 0.0526, wR 2 = 0.1288