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Synthesis 2004(15): 2445-2448  
DOI: 10.1055/s-2004-831222
PAPER
© Georg Thieme Verlag Stuttgart · New York

Cis-Carbocupration of Acetylenic Phosphine Oxides and Its Application in the Stereoselective Synthesis of Polysubstituted Vinyl Phosphine Oxides

Xian Huang*a,b, Zhimeng Wua
a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. China
Fax: +86(571)88807077; e-Mail: huangx@mail.hz.zj.cn;
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Publication History

Received 12 May 2004
Publication Date:
16 September 2004 (online)

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Abstract

Bisubstituted or 1,2,2-trisubstituted vinyl phosphine oxides were prepared stereoselectively by the carbocupration of acetylenic phosphine oxides followed by hydrolysis or by reacting with other electrophiles.

Keywords

carbocupration - acetylenic phosphine oxide - polysubstituted vinyl phosphine oxides

18

Crystal Data for 4g: C25H25OP, MW = 372.45, monoclinic, space group, P21/n, a = 19.002(4), b = 6.305(2), c = 18.514(6) Å, β = 110.66(2)o, V = 2075(1) Å3, T = 293K, Z = 4, Dc = 1.92 g·cm-1, µ = 1.44 mm-1, λ = 0.71069 Å, F(000) = 792.00, independent reflections (R int = 0.000), 8478 reflections collected; refinement method, full-matrix least-squares refinement on F2; goodness-of-fit on F ² = 0.223; Final R indices [ I > 2 σ (I)] R1 = 0.050, wR2 = 0.094.