A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols

Abstract

Abstract:Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio-and enantio-selectivity (up to 99% ee). This modular combination, including Jones oxidation and asymmetric organocatalysis, has satisfactory compatibility and reliability even at a 20 mmol scale, albeit without intermediary purification.

Highly Efficient One‐pot Aerobic Synthesis of α‐Aminophosphonate from Alcohols: Dual Catalytic Effect of Tetrabutylammonium Tribromide (TBATB)

“…This strategy is a good model in industrial processes because it reduces costs, time and waste generation. [22][23][24][25][26][27] Orange crystalline solid TBATB is known as a mild and efficient agent for bromination of alkenes, alkynes, synthesis of α-bromo acetals, condensation of carbonyl compounds, regioselective bromination of aromatic amines, selective bromina-tion of phenols, preparation of α-bromo enones, determination of unsaturation number, catalytic protection-deprotection of carbonyl compounds, oxidizing bromination, and oxidation of benzyl alcohols, aliphatic aldehydes, sulfoxides, and amino acids. [28][29][30][31][32][33][34] Very recently, we presented TBATB as an agent for alcohol and toluene oxidation under visible blue light irradiation (465 nm) under mild and green conditions.…”