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Synlett 1993; 1993(10): 788-790
DOI: 10.1055/s-1993-22610
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Stereochemically Pure Allylmetals: An Application to Diastereoselective γ-Allylation of Aldehydes

Shigeki Habaue* , Katsutaka Yasue, Akira Yanagisawa, Hisashi Yamamoto
  • *School of Engineering, Nagoya University, Chikusa, Nagoya 464-01, Japan
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Publication Date:
19 March 2002 (online)

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A new methodology, the preparation of stereochemically homogeneous allylic metals (Mg and Ba) from the corresponding allylic chlorides, was successfully applied to a diastereoselective γ-allylation reaction of aldehydes using B-methoxy-9-borabicyclo[3.3.1]nonane (B-OMe-9-BBN) as an additive. Using this method, threo-homoallylic alcohols were selectively obtained from (E)-allylic metal compounds and erythro-isomers from (Z)-allylic metal compounds in high yields.

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