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Synthesis 2000; 2000(6): 775-777
DOI: 10.1055/s-2000-6272
short paper
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Stereoselective Preparation of α-Heteroatom Substituted α,β-Unsaturated Ketones

Aiming Sun* , Xian Huang
  • *Department of Chemistry, Zhejiang University, Xi-xi Campus, Hangzhou, 310028, P.R. China; Fax +86 (5 71) 8 80 70 77; E-mail: huangx@mail.hz.zj.cn
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Publication History

Publication Date:
31 December 2000 (online)

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(E)-α-Selanylvinylzirconium and (E)-α-silylvinylzirconium complexes 2 were prepared conveniently via hydrozirconation of the alkynylselenides and the alkynylsilanes 1, respectively. Intermediates 2 were reacted with acyl chlorides 3 via Zr-Cu transmetalation with retention of the configuration to afford α-seleno or α-silyl α,β-unsaturated ketones 4 in good yield.

alkynylselenides - alkynylsilanes - hydrozirconation - Zr-Cu transmetallation - α-heteroatom substituted α,β-unsaturated ketones - acylations

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