Enantioselective allenylation of aldehydes via Brønsted acid catalysis
M Wang, S Khan, E Miliordos… - Advanced Synthesis & …, 2018 - Wiley Online Library
Advanced Synthesis & Catalysis, 2018•Wiley Online Library
An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric
acid was reported. Under the developed conditions, 1, 1′‐disubstituted allenic alcohols
were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to
probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol
moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was
supported by experimental data.
acid was reported. Under the developed conditions, 1, 1′‐disubstituted allenic alcohols
were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to
probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol
moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was
supported by experimental data.
Abstract
An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric acid was reported. Under the developed conditions, 1,1′‐disubstituted allenic alcohols were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was supported by experimental data.
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