Hydrozirconation of Allenylstannane for Generating Bimetallic Three-Carbon Species: Synthesis of (E)-1,3-Dienes from Carbonyl Compounds

Hideki Maeta; Takayuki Hasegawa; Keisuke Suzuki

doi:10.1055/s-1993-22448

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Synlett 1993; 1993(5): 341-343
DOI: 10.1055/s-1993-22448

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Hydrozirconation of Allenylstannane for Generating Bimetallic Three-Carbon Species: Synthesis of (E)-1,3-Dienes from Carbonyl Compounds

Hideki Maeta^* , Takayuki Hasegawa, Keisuke Suzuki

^*Department of Chemistry, Keio University, Hiyoshi, Yokohama 223, Japan

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Publication Date:
19 March 2002 (online)

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Hydrozirconation of allenylstannane 4 generates (E) allylzirconocene species 5 with a γ-Bu₃Sn substituent. This species reacts with aldehydes and ketones in highly regio- and stereoselective manner, and subsequent in situ-treatment with BF₃·OEt₂ (or CF₃COOH) effects the β-elimination to give terminal 1,3-dienes with high (E) selectivity. Mechanistic rationale is proposed for the high geometrical selectivity.

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