Organocatalytic Domino Michael-Aldol Reaction of Ketones and alpha,beta-Unsaturated Trifluoromethyl Ketones

摘要

Pyrrolidine-catalyzed domino Michael-aldol reaction of alpha,beta-unsaturated trifluoromethyl ketones and ketones was achieved under mild conditions; beta-hydroxy-beta-trifluoromethyl cyclohex-anones were obtained in high yields with good diastereoselectivi-ties.The importance of fluorine-containing compounds in the fields of agricultural, medicinal and material chemistry is well known.1 Among various organofluorine compounds, a-trifluoromethyl tertiary alcohols have attracted much attention recently because they could serve as liquid crystals23 and drugs such as Efavirenz (anti-HIV). On the other hand, since cyclic compounds form the backbone of many bioactive compounds, the development of synthetic methods for cyclic a-trifluoromethyl tertiary alcohols would be very valuable in the field of pharmaceutical research.