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  • Title: trans-hydroalumination/alkylation: one-pot synthesis of trisubstituted allylic alcohols.
    Author: Langille NF, Jamison TF.
    Journal: Org Lett; 2006 Aug 17; 8(17):3761-4. PubMed ID: 16898811.
    Abstract:
    [reaction: see text] Described herein is a method of stereoselective synthesis of trisubstituted allylic alcohols by alkylation of alkenyl alanates, formed in situ through treatment of propargyl alcohols with Vitride (Red-Al). This technique represents the first of its kind to feature a trans-hydrometalation, and is particularly effective for the formation of 1,4-dienes. Applications involving primary, secondary, and tertiary alcohols are discussed, as well as limitations regarding both alkyne and electrophile components.
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