Lou, Sha; Moquist, Philip N.; Schaus, Scott E. published the article 《Asymmetric Allylboration of Acyl Imines Catalyzed by Chiral Diols》. Keywords: asym allylboration acyl imine chiral diol catalysis.They researched the compound: (S)-3,3′-Dibromo-1,1′-bi-2-naphthol( cas:119707-74-3 ).Application of 119707-74-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:119707-74-3) here.
Chiral BINOL-derived diols catalyze the enantioselective asym. allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3′-Ph2-BINOL (the most effective catalyst) as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products were obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines, e.g. 87 % (99:1 enantiomer ratio) N-((R)-1-phenylbut-3-enyl)benzamide from diisopropyl allylboronate and N-(benzylidene)benzamide. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) were obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asym. transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic studies of the allylboration reaction including IR, NMR, and mass spectrometry studies indicate that acyclic boronates are activated by chiral diols via exchange of one of the boronate alkoxy groups with activation of the acyl imine via H bonding.
In addition to the literature in the link below, there is a lot of literature about this compound((S)-3,3′-Dibromo-1,1′-bi-2-naphthol)Application of 119707-74-3, illustrating the importance and wide applicability of this compound(119707-74-3).
Reference:
Bromide – Wikipedia,
bromide – Wiktionary