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  • Title: Rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated amides.
    Author: Sakuma S, Miyaura N.
    Journal: J Org Chem; 2001 Dec 28; 66(26):8944-6. PubMed ID: 11749626.
    Abstract:
    The conjugate addition of arylboronic acids to alpha,beta-unsaturated amides was carried out in the presence of a chiral rhodium catalyst and an aqueous base. The catalyst prepared in situ from Rh(acac)(CH(2)=CH(2))(2) and (S)-binap provided (R)-N-benzyl-3-phenylbutanamide with 93% ee in the addition of phenylboronic acid to N-benzyl crotonamide. The reaction suffered from incomplete conversion resulting in moderate yields, but addition of an aqueous base, such as K(2)CO(3) (10-50 mol%) was found to be highly effective to improve the chemical yields. The role of the base giving a RhOH species active for transmetalation with arylboronic acids was discussed.
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