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Catalytic asymmetric synthesis of Secondary (E)-allyl alcohols from acetylenes and aldehydes via (1-alkenyl)zinc intermediates. Preliminary Communication

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Oppolzer, Wolfgang
Published in Helvetica Chimica Acta. 1992, vol. 75, no. 1, p. 170-173
Abstract 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).
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Other version: http://doi.wiley.com/10.1002/hlca.19920750114
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OPPOLZER, Wolfgang, RADINOV, Roumen Nikolaev. Catalytic asymmetric synthesis of Secondary (E)-allyl alcohols from acetylenes and aldehydes via (1-alkenyl)zinc intermediates. Preliminary Communication. In: Helvetica Chimica Acta, 1992, vol. 75, n° 1, p. 170-173. https://archive-ouverte.unige.ch/unige:85071

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