928826-52-2

Upstream product

• 75553-25-2 (E)-2-Methyl-5-phenyl-2-penten-1-ol 
• 75553-24-1 (Z)-2-methyl-5-phenylpent-2-en-1-ol 
• 116760-89-5 (Z)-methyl 2-methyl-5-phenylpent-2-enoate 
• 70925-46-1 (2E)-2-methyl-5-phenyl-2-pentenal 
• 114377-78-5 ethyl (E)-2-methyl-5-phenyl-pent-2-enoate 
• 928826-43-1 2-methyl-3-phenethyl-oxirane-2-carboxylic acid (4-dimethylamino-phenyl)-amide 

Relevant academic research and scientific papers

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Catalytic asymmetric epoxidation of α-branched enals

An asymmetric catalytic epoxidation of α-branched, α,β-unsaturated aldehydes is presented. A highly synergistic combination of a primary cinchona-based amine and a chiral phosphoric acid was found to promote the reaction with excellent enantiocontrol for α-monosubstituted and α,β-disubstituted enals.

Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated anilides as ester surrogates

Catalytic asymmetric epoxidation of α-methyl α,β- unsaturated carboxylic acid derivatives was achieved using anilide as a template. The Pr(Oi-Pr)3-6,6?-Ph-BINOL complex (10 mol%) with a Ph3P(O) (30 mol%) additive promoted the epoxida

Synthetic studies on the sarcodictyins: Synthesis of fully functionalized cyclization precursors

A strategy featuring a key retrosynthetic disconnection at the C2-C3 position was applied to the total synthesis of the common diterpenoid tricyclic skeleton of sarcodictyins and eleutherobin. Fully functionalized cyclization precursors were accessed via a brief and convergent route, making use of unprecedented synthetic transformations.