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  • Title: Highly enantioselective vinyl additions of vinylaluminum to ketones catalyzed by a titanium(IV) catalyst of (S)-BINOL.
    Author: Biradar DB, Gau HM.
    Journal: Org Lett; 2009 Feb 05; 11(3):499-502. PubMed ID: 19117491.
    Abstract:
    We report a novel asymmetric addition of vinyl group to ketones using vinylaluminum reagents catalyzed by in situ prepared Ti(O(i)Pr)(4) complexes of (S)-BINOL to afford diversified tertiary allylic alochols. Varieties of aromatic ketones bearing either an electron-donating or an electron-withdrawing substituent on the aromatic ring were examined to afford products in excellent enantioselectivities of up to 98% ee with high yields. A 10-fold scale-up reaction afforded the product in a similar yield with a comparable enantioselectivity. More importantly, additions of a variety of vinyl reagents including functionalized vinyls were demonstrated, affording tertiary allylic alcohols with good to excellent enantioselectivities of up to 96% ee.
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