Parts-per-million level loading organocatalysed enantioselective silylation of alcohols

摘要

The field of organocatalysis has blossomed over the past few decades, becoming an alternative to transition-metal catalysis or even replacing the realm of transition-metal catalysis. However, a truly powerful organocatalyst with a high turnover number (TON) and turnover frequency (TOF) while retaining high enantioselectivity is yet to be discovered. Similar to metal catalysis, extremely low catalyst loading (p.p.m. or p.p.b. levels) is the ultimate goal of the organocatalysis community. Herein we report a remarkable contribution in this context: 1 p.p.m. loading of a simple 1,1′-bi-2-naphthol-based organocatalyst was enough to achieve highly enantioselective silylation reactions of alcohols. The unprecedented TONs and excellent enantioselectivity are ascribed to the robustness of the catalyst and systematic cooperative hydrogen-bonding organocatalysis in a densely confined chiral space.