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

1 January 1993

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1993 (05) , 341-343
https://doi.org/10.1055/s-1993-22448

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.

Keywords

ALLENYLSTANNANE
DIENES
HYDROZIRCONATION
TREATMENT
EM CLASS
BOLD
REACTS
GIVE
TERMINAL

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