284686-91-5

Upstream product

• 252058-33-6 2-(4-methoxyphenyl)propanal 
• 105-53-3 diethyl malonate 
• 2901-41-9 2-(4-methoxyphenyl)ethyl propionate 
• 14062-18-1 ethyl p-methoxyphenylacetate 
• 93397-63-8 2-(4-methoxyphenyl)propan-1-ol 

Relevant academic research and scientific papers

The catalytic asymmetric Knoevenagel condensation

116 years after the discovery of the Knoevenagel condensation, the first catalytic asymmetric variant has been developed. Dynamic kinetic resolution in the reaction of α-branched aldehydes with malonates in the presence of a newly designed and readily available modified cinchona amine catalyst gives the corresponding alkylidene malonates in high enantioselectivity (see scheme).

1,2-asymmetric induction in the conjugate addition of organocopper reagents to γ-aryl α,β-unsaturated carbonyl derivatives

The diastereoselectivity in the conjugate addition of organocopper reagents to γ-aryl α,β-unsaturated carbonyl derivatives 8-14 was investigated. The syn-diastereoselectivity was obtained irrespective of the reagents type in the addition of 8, while the anti-diastereoselectivity was obtained in the addition of 10-14 with RCu and RCu(CN)Li (R=Me and Bu) and the syn-selectivity was produced in the addition of 10-14 with R2CuLi and R2Cu(CN)Li2. The reagent controlled and substrate dependent diastereoselectivity are explained by two different reaction pathways: either π-complex formation or ordinary nucleophilic addition. Reduction potentials of the Michael acceptors and electron donating ability of organocopper reagents control the reaction pathway. (C) 2000 Elsevier Science Ltd.