1000681-33-3Relevant academic research and scientific papers
A catalytic asymmetric borono variant of Hosomi-Sakurai reactions with N,O-aminals
Huang, Yi-Yong,Chakrabarti, Ananya,Morita, Naohide,Schneider, Uwe,Kobayashi, Sha
supporting information; experimental part, p. 11121 - 11124 (2012/02/02)
Aminal attraction: The combination of indium(I) chloride and a chiral silver binol phosphate provides an excellent catalyst for asymmetric Hosomi-Sakurai reactions between N,O-aminals and boronates (see scheme; PG=protecting group, pin=pinacolato). The su
Asymmetric allylboration of acyl imines catalyzed by chiral diols
Lou, Sha,Moquist, Philip N.,Schaus, Scott E.
, p. 15398 - 15404 (2008/09/18)
Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3′-Ph2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) are obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asymmetric transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic investigations 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 hydrogen bonding.
