Highly Enantioselective 3-Furylation of Ketones Using (3-Furyl)titanium Nucleophile

A novel asymmetric 3-furyl addition of (3-furyl)Ti(OiPr)3 to ketones in the presence of 10 mol % (S)-BINOL is reported. The catalytic system works excellently for aromatic ketones, α- or β-halophenones, α,β-unsaturated ketones, and acetylfuran, affording products in high yields with excellent enantioselectivities of up to 97% ee.

本研究报道了一种新型不对称3-呋喃基加成反应：在10 mol%的(S)-联萘酚((S)-BINOL)存在下，(3-呋喃基)三异丙氧基钛((3-furyl)Ti(OiPr)3)与酮类化合物发生加成反应。该催化体系对芳香酮、α-或β-卤代芳酮、α,β-不饱和酮以及乙酰呋喃均具有优异的催化活性，可获得高收率的目标产物，且对映选择性极佳，最高对映体过量(ee)值可达97%。