Silylcupration of 1-Alkynylphosphine Oxides: Stereo- and Regioselective Synthesis of β-Silyl Substituted Vinylphosphine Oxides

Xian Huang; Lubin Xu

doi:10.1055/s-2005-924763

PAPER

Silylcupration of 1-Alkynylphosphine Oxides: Stereo- and Regioselective Synthesis of β-Silyl Substituted Vinylphosphine Oxides

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

Abstract

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Abstract

β-Silyl substituted vinylphosphine oxides were prepared stereo- and regioselectively by the silylcupration of 1-alkynylphosphine oxides followed by hydrolysis or by reacting with other electrophiles.

Key words

silylcupration - 1-alkynylphosphine oxide - β-silyl substituted vinylphosphine oxides

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References

<A NAME="RF09405SS-1A">1a</A> Trost BM. Fleming I. Semmelhack MF. In Comprehensive Organic Synthesis Vol. 4: Pergamon; New York: 1991.

<A NAME="RF09405SS-1B">1b</A> Normant JF. Alexakis A. Synthesis 1981, 841

<A NAME="RF09405SS-2A">2a</A> Posner GH. Org. React. 1974, 22: 253

<A NAME="RF09405SS-2B">2b</A> Normant JF. Synthesis 1972, 63

<A NAME="RF09405SS-3A">3a</A> Corey EJ. Katzenellenbogen JA. J. Am. Chem. Soc. 1969, 91: 1851

<A NAME="RF09405SS-3B">3b</A> Fiandanese V. Marchese G. Naso F. Tetrahedron Lett. 1978, 5131

<A NAME="RF09405SS-3C">3c</A> Gil JO. Oh DY. J. Org. Chem. 1999, 64: 2950

<A NAME="RF09405SS-3D">3d</A> Braga AL. Reckziegel A. Silvera CC. Comasseto JV. Synth. Commun. 1994, 1165

<A NAME="RF09405SS-3E">3e</A> Chechik-Lankin H. Marek I. Org. Lett. 2003, 5: 5087

<A NAME="RF09405SS-4A">4a</A> Huang X. Duan DH. Chem. Commun. 1999, 1741

<A NAME="RF09405SS-4B">4b</A> Huang X. Liang CG. Xu Q. He QW. J. Org. Chem. 2001, 66: 74

<A NAME="RF09405SS-5">5</A> Xie MH. Huang X. Synlett 2003, 477

<A NAME="RF09405SS-6">6</A> Huang X. Wu ZM. Synthesis 2004, 2445

<A NAME="RF09405SS-7A">7a</A> Huang X. Xie MH. Org. Lett. 2002, 4: 1331

<A NAME="RF09405SS-7B">7b</A> Huang X. Xie M. J. Org. Chem. 2002, 67: 8895

For a review on synthetic uses of vinylphosphonates, see:

<A NAME="RF09405SS-8A">8a</A> Minami T. Motoyoshiya J. Synthesis 1992, 333

For biological uses, see, for example:

<A NAME="RF09405SS-8B">8b</A> Kawamoto AP. Campbell MM. J. Chem. Soc., Perkin Trans. 1 1997, 1249

<A NAME="RF09405SS-8C">8c</A> Gao J. Martichonok V. Whitesides GM. J. Org. Chem. 1996, 61: 9538

<A NAME="RF09405SS-9A">9a</A> Bardels B. Clayden J. Martin CG. Neslson A. Russel MG. Warren S. J. Chem. Soc., Perkin Trans.1 1999, 1807

<A NAME="RF09405SS-9B">9b</A> Clayden J. Neslson A. Warren S. Tetrahedron Lett. 1997, 38: 3471

<A NAME="RF09405SS-10A">10a</A> Brandi A. Cannavò P. Pietrusiewicz KM. Zablocka M. Wieczorek M. J. Org. Chem. 1989, 54: 3073

<A NAME="RF09405SS-10B">10b</A> Brandi A. Cicchi S. Goti A. Pietrusiewicz KM. Zablocka M. Wieczorek M. J. Org. Chem. 1991, 56: 4383

<A NAME="RF09405SS-11">11</A> Nicolaou KC. Maligres P. Shin J. de Leon E. Rideout D. J. Am. Chem. Soc. 1990, 112: 7825

<A NAME="RF09405SS-12A">12a</A> Fleming I. Roessler F. J. Chem. Soc., Chem. Commun. 1980, 276

<A NAME="RF09405SS-12B">12b</A> Fleming I. Newton TW. Roessler F. J. Chem. Soc., Perkin Trans. 1 1981, 2527

<A NAME="RF09405SS-12C">12c</A> Fleming I. Taddei M. Synthesis 1985, 899

<A NAME="RF09405SS-12D">12d</A> Fleming I. Martinez de Marigorta E. Tetrahedron Lett. 1993, 34: 1201

<A NAME="RF09405SS-12E">12e</A> Fleming I. Martinez de Marigorta E. J. Chem. Soc., Perkin Trans. 1 1999, 889

<A NAME="RF09405SS-12F">12f</A> Chen H.-M. Oliver JP. J. Organomet. Chem. 1986, 316: 255

<A NAME="RF09405SS-12G">12g</A> Millar JG. Tetrahedron Lett. 1989, 30: 4913

<A NAME="RF09405SS-12H">12h</A> Capella L. Degl’Innocenti A. Reginato G. Ricci A. Taddei M. J. Org. Chem. 1989, 54: 1473

<A NAME="RF09405SS-12I">12i</A> Casarini A. Jousseaume B. Lazzari D. Porciatti E. Reginato G. Ricci A. Seconi G. Synlett 1992, 981

<A NAME="RF09405SS-12J">12j</A> Capella L. Capperucci A. Curotto G. Lazzari D. Dembech P. Reginato G. Ricci A. Tetrahedron Lett. 1993, 34: 3311

<A NAME="RF09405SS-12K">12k</A> Reginato G. Mordini A. Valacchi M. Grandini E. J. Org. Chem. 1999, 64: 9211

<A NAME="RF09405SS-12L">12l</A> Barbero A. Blanco Y. García C. Pulido FJ. Synthesis 2000, 1223

<A NAME="RF09405SS-13A">13a</A> Barbero A. García C. Pulido FJ. Tetrahedron 2000, 56: 2739

<A NAME="RF09405SS-13B">13b</A> Barbero A. García C. Pulido FJ. Fleming I. Tetrahedron Lett. 1999, 40: 6649

<A NAME="RF09405SS-14">14</A> The cleavage of epoxysilanes with lithium diphenylphosphide can also afford β-silylvinylphosphine oxides, see: Cuadrado P. González-Nogal AM. Sarmentero MA. Chem. Eur. J. 2004, 10: 4491

<A NAME="RF09405SS-15">15</A> Charrier C. Chodkiewicz W. Cadiot P. Bull. Soc. Chim. Fr. 1966, 1002

For Me₃SiLi, see:

<A NAME="RF09405SS-16A">16a</A> Still WC. J. Org. Chem. 1976, 41: 3063

For PhMe₂SiLi, see:

<A NAME="RF09405SS-16B">16b</A> Fleming I. Roberts RC. Smith SC. J. Chem. Soc., Perkin Trans. 1 1998, 1209

<A NAME="RF09405SS-17">17</A> For reviews on vinylic selenides and tellurides - preparation, reactivity, and their synthetic applications, see: Comasseto JV. Ling LW. Petragnani N. Stefani HA. Synthesis 1997, 373

<A NAME="RF09405SS-18">18</A> Dyba M. Jezowska-Bojczuk M. Kiss E. Kiss T. Kozlowski H. Leroux Y. Manouni DEl. J. Chem. Soc., Dalton Trans. 1996, 1119