112348-14-8Relevant academic research and scientific papers
1,2-asymmetric induction in the conjugate addition of organocopper reagents to γ-aryl α,β-unsaturated carbonyl derivatives
Chounan, Yukiyasu,Ono, Yasuo,Nishii, Shinji,Kitahara, Haruo,Ito, Shoei,Yamamoto, Yoshinori
, p. 2821 - 2831 (2007/10/03)
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.
