737817-72-0Relevant academic research and scientific papers
Substituent effect on the diastereoselectivity in the chelation-controlled radical reactions of γ-(p-substituted-benzyloxy)-α-methylene esters with alkyl iodides
Yajima, Tomoko,Okada, Kyoko,Nagano, Hajime
, p. 5683 - 5693 (2004)
A pronounced substituent effect on the diastereoselectivity in the chelation controlled radical reactions of ethyl γ-(p-substituted- benzyloxy)-α-methylenecarboxylates with alkyl iodides was observed. The syn-selectivity increased in the order of electron-donating ability NO 231H NMR spectroscopy and the competition experiments between p-isopropylbenzyloxy and p-trifluoromethylbenzyloxy esters showed that the electron-donating p-isopropyl group stabilized the seven-membered chelate ring to give high syn-selectivity.
