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

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

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1993

Year

Hideki Maeta, T. Hasegawa, Keisuke Suzuki

Carbonyl CompoundsChemical EngineeringEngineeringHigh Geometrical SelectivityBimetallic Three-carbon SpeciesAllylzirconocene Species 5Organic ChemistryStereoselective SynthesisChemistryAllenylstannane 4Synthetic ChemistryEnantioselective Synthesis

Abstract

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.