Asymmetric 1,4-Addition of Diarylphosphine Oxides to α, β-Unsaturated 2-Acyl Imidazoles
Lirong Chen1, Guiyong Wang2, Xiufei Nong2
1Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, 2929 Yuehua road, Kunming, 650500, China.
Abstract:
Here we introduce a metal-free, catalytic and enantioselective strategy from α,β-unsaturated 2-acyl imidazoles to the chiral phosphorous 2-acyl imidazoles. Interestingly, this methodology was catalyzed by the classical and commercial oxazaborolidine under mild conditions. This strategy features a wide range of substrates scope with good yields and excellent enantioselectivities. The possible mechanism further suggests the key of this reaction through the cleavage of diarylphosphine oxides using Frustrated Lewis Pairs theory.
Related Concept Videos
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction


