CuF-Catalyzed Enantioselective Arylation and Alkenylation: Novel Synthetic Approach to SM-130686

摘要

Chiral allylic alcohols are among the most versatile synthetic intermediates. Previously, in the presence of DTBM-SEGPHOS -CuF catalyst (3-10 mol %), we developed a new catalytic enantioselective process for chiral allylic alcohol and diarylmethanol synthesis using air- and moisture-stable alkenylsilanes and phenylsilane as nucleophiles . In view of wide availability of boron reagents, we also developed reactions using alkenylboronates and arylboronates as nucleophiles. Appropriate choice of additives enabled a new entry to catalytic enantioselective alkenylation and arylation with high efficiency (Scheme 1)). The key to success partly involves the accelerated regeneration of reactive alkenylcopper and arylcopper through transmetalation from the silylated or borylated nucleophiles.