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Publication 167  

  1. Catalytic asymmetric synthesis of Secondary (E)-allyl alcohols from acetylenes and aldehydes via (1-alkenyl)zinc intermediates. Preliminary Communication
    Oppolzer, W.; Radinov, R. N.
    Helv. Chim. Acta 1992, 75, 170-173

Hydroboration of aliphatic 1-alkynes with freshly prepared dicyclohexylborane (1 mol-equiv., hexane), treatment of the resulting [(E)-1-alkenyl]boranes 5 with Et2Zn or Me2Zn (1.05 mol-equiv.) followed by addition of (−)-3-exo-(dimethylamino)isoborneol (DAIB, 8; 0.01 mol-equiv.), subsequent addition of a solution of an aromatic or aliphatic aldehyde (1 mol-equiv., hexane), and quenching with aq. NH4Cl provided (E)-allyl alcohols 6 usually in 70–95% yield with 79–98% enantiomeric excess (Scheme 3 and Table).

DOI : 10.1002/hlca.19920750114 

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