Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Weixin  Zheng; Xian  Huang

doi:10.1055/s-2002-35624

PAPER

Stereoselective Preparation of (Z)-γ-Silyl-γ,δ-Unsaturated Ketones and their Application in the Synthesis of 1,4-Diketones

Weixin Zheng^a, Xian Huang*^a,b
^a Department of Chemistry, Zhejiang University (Xixi Campus, Hangzhou 310028, P. R. China
^b The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, P. R. China
e-Mail: huangx@mail.hz.zj.cn;

Abstract

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Abstract

Hydrozirconation reaction of alkynylsilanes 1 followed by Michael addition to α,β-unsaturated ketones in the presence of CuBr·Me₂S complex produced (Z)-γ-silyl-γ,δ-unsaturated ketones 3 stereoselectively. 1,4-Diketones were prepared via epoxidation and hydrolysis of 3.

Key words

silicon - zirconium - Michael additions - ketones - enones - alkynes

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References

<A NAME="RF05602SS-1A">1a</A> Fleming I. Dunogues J. Smithers RH. Org. React. 1989, 37: 57

<A NAME="RF05602SS-1B">1b</A> Fleming I. Barbero A. Walter D. Chem. Rev. 1997, 97: 2063

<A NAME="RF05602SS-2">2</A> Ellison RA. Synthesis 1973, 397

<A NAME="RF05602SS-3">3</A> Mikami K. Kishi N. Nakai T. Chem. Lett. 1982, 1643

<A NAME="RF05602SS-4">4</A> Sato F. Watanabe H. Tanaka Y. Xamas T. Tetrahedron Lett. 1983, 24: 1041

<A NAME="RF05602SS-5A">5a</A> Huang X. Xu X. Zheng W. Synth. Commun. 1999, 29: 2399

<A NAME="RF05602SS-5B">5b</A> Sun A. Huang XJ. Synthesis 2000, 775

<A NAME="RF05602SS-6">6</A> Hudlicky T. Price JD. Chem. Rev. 1989, 89: 1467

<A NAME="RF05602SS-7A">7a</A> Stetter H. Schreckenberg M. Chem. Ber. 1974, 107: 2453

<A NAME="RF05602SS-7B">7b</A> Stetter H. Angew. Chem., Int. Ed. Engl. 1976, 15: 639

<A NAME="RF05602SS-7C">7c</A> Stetter H. Jonas F. Chem. Ber. 1981, 114: 564

<A NAME="RF05602SS-8A">8a</A> Kel’in AV. Kulinkovich OG. Synthesis 1996, 330

<A NAME="RF05602SS-8B">8b</A> Nebar NM. Kel’in AV. Kulinkovich OG. Synthesis 2000, 1259

<A NAME="RF05602SS-9A">9a</A> Duus F. Tetrahedron 1976, 32: 2847

<A NAME="RF05602SS-9B">9b</A> Chiu P. Sammes MP. Tetrahedron 1988, 44: 3531

<A NAME="RF05602SS-10">10</A> Yasuda M. Tsuji S. Shibata I. Baba A. J. Org. Chem. 1997, 62: 8282

CCDC-189354 contains the supplementary crystallographic data for this paper.

<A NAME="RF05602SS-12">12</A> Yamaguchi R. Kawsaki H. Kawanisi M. Synth. Commun. 1982, 12: 1027

<A NAME="RF05602SS-13">13</A> Seebach D. Angew. Chem., Int. Ed. Engl. 1979, 18: 239

<A NAME="RF05602SS-14">14</A> Uchida K. Utimoto K. Nozaki H. J. Org. Chem. 1976, 41: 2216

<A NAME="RF05602SS-15">15</A> Kohler EP. Chadwell HM. Org. Synth., Coll. Vol. I Wiley; London: 1951. p.78

<A NAME="RF05602SS-16">16</A> Corbett RE. Davey CL. J. Chem. Soc. 1955, 291

<A NAME="RF05602SS-17">17</A> House HO. Chu Y. Wilkins JM. Umen MJ. J. Org. Chem. 1975, 40: 1460

<A NAME="RF05602SS-18">18</A> Hart DW. Schwartz J. J. Am. Chem. Soc. 1974, 96: 8115

<A NAME="RF05602SS-19">19</A> Arcadi A. Rossi E. Tetrahedron 1998, 54: 15253

<A NAME="RF05602SS-20">20</A> Katritrky AR. Yang ZJ. Lam JN. J. Org. Chem. 1991, 56: 6917

<A NAME="RF05602SS-21">21</A> Katritzky AR. Lang H. Wang Z. Lie Z. J. Org. Chem. 1996, 61: 7551