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  • Title: Highly diastereoselective and enantioselective preparation of homoallylic amines: application for the synthesis of beta-amino acids and gamma-lactams.
    Author: Ramachandran PV, Burghardt TE.
    Journal: Chemistry; 2005 Jul 18; 11(15):4387-95. PubMed ID: 15880541.
    Abstract:
    Reactions of N-silyl- and N-aluminoimines with B-allyldiisopinocampheylborane in the presence of methanol, followed by oxidative workup furnished homoallylic amines in good yields and high ee. A 11B NMR spectroscopy study revealed that the reactions do not proceed, even at room temperature, unless a molar equivalent of water or methanol is added. The first reagent-controlled asymmetric crotylboration and alkoxyallylboration of aldimines furnishing beta-methyl or beta-alkoxy homoallylic amines in very high diastereoselectivity and enantioselectivity are reported herein. Crotylboration and alkoxyallylboration of imines proceed only with the "allyl"-boron "ate" complexes, instead of the "allyl"-dialkylboron reagents used with aldehydes. The addition of methanol is necessary for these reactions as well. Application of this methodology for the conversion of representative nitriles to beta-amino acids in two steps has been described. Additionally, a procedure for the preparation of chiral delta-amino alcohols and gamma-lactams from nitriles is also reported.
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