Synthesis of Optically Pure 2-Substituted 1,3-Propanediol Spiroacetal Derivatives of l-Menthone via Hydroboration-Coupling Sequence

Yoshihiro Nomoto; Norio Miyaura; Akira Suzuki

doi:10.1055/s-1992-21470

Synlett 1992; 1992(9): 727-729
DOI: 10.1055/s-1992-21470

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Synthesis of Optically Pure 2-Substituted 1,3-Propanediol Spiroacetal Derivatives of l-Menthone via Hydroboration-Coupling Sequence

Yoshihiro Nomoto^* , Norio Miyaura, Akira Suzuki

^*Department of Applied Chemistry, Faculty of Engineering, Hokkaido University, Sapporo 060, Japan

Abstract

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Hydroboration of the exo-methylene acetal of l-menthone (1) with 9-borabicyclo[3.3.1]nonene (9-BBN) occurs by axial attack of borane reagents to give the equatorial isomer of 9-alkyl-9-BBN derivative 2 diastereoselectively. The cross-coupling reaction of the alkylborane 2 thus obtained with a variety of organic halides provides 2-substituted 1,3-propanediol spiroacetal derivatives of l-menthone 3 which are useful synthetic precursors of optically active compounds. The utility of this reaction is demonstrated by the synthesis of highly pure (2S)-2-methyl-3-phenylpropanol (9).

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