166940-18-7

Upstream product

• 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 
• 75553-25-2 (E)-2-Methyl-5-phenyl-2-penten-1-ol 
• 166661-71-8 ((2R,3R)-2-Methyl-3-phenethyl-oxiranyl)-methanol 

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.

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.