Catalytic Nucleophilic Addition of 3, 5-Dialkyl-4-nitroisoxazoles to Trifluoromethyl Ketones on Water

Abstract

The triethylamine catalyzed nucleophilic addition of 3,5-dialkyl-4-nitroisoxazoles to trifluoromethyl ketones on water has been realized affording trifluoromethyl tertiary alcohol derivatives in 66%～99% yields. The products were easily transformed to the resulting alkenes by dehydration or acids by oxidation.

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF3 tertiary alcohols

“…Significantly, the key intermediate of platelet-activating factor antagonist IV ( 3aa ) could be obtained by this protocol in one step without using strongly oxidizing reagents. Compared with the protocol reported by Liu's group, 22 this protocol has higher atom economy and high commercial potential. We then used our strategy to synthesize 4ab , a key intermediate of the iso-oxaline veterinary insecticide fluralaner, in a two-step process that has a shorter synthetic route than previously reported methods 23 and avoids the use of costly Zn(OMe) 2 and environmentally harmful O 3 and SMe 2 .…”

3-Trifluoroacetyl-quinolin-2(1H)-ones as Carbonyl and Acid Surrogates in the Passerini-/Ugi-Type Reaction

“…In particular, the demand for the introduction of a trifluoromethyl group at a strategic position has been increasing rapidly . In this connection, α-trifluoromethyl, α-hydroxy carboxamides have attracted much attention on account of their promising medicinal properties . As shown in Figure a, these core structures are entrenched in many of the biologically active compounds such as inhibitors of pyruvate dehydrogenase kinase ( I ), peptidomimetic inhibitors ( II ), and a soluble guanylate cyclase stimulator (olinciguat) ( III ) …”

Organocatalytic enantioselective cross-aldol reaction of aryl ketones with heteroaromatic trifluoromethyl ketone hydrates for the synthesis of α-trifluoromethyl tertiary alcohols

“…1, including efavirenz, 6 a commercial anti-HIV drug, and other anti-HIV compounds I and II . 7 Other examples include compound III , 8 a platelet activating factor antagonist, and the non-steroidal glucocorticoid agonist IV . 9 Consequently, the development of facile and convenient synthetic routes to these α-trifluoromethyl tertiary alcohols is of high interest and substantial efforts have been made to produce them in a catalytically enantioselective manner.…”