138380-98-0Relevant academic research and scientific papers
A Model Study of Intramolecular Asymmetric Radical Cyclizations of a-Ester and α-Amide Radicals
Yeh, Ru-Long,Jiaang, Weir-Torn,Tsai, Yeun-Min
, p. 253 - 260 (2007/10/03)
Starting from malonate, a practical route was developed for the synthesis of α-phenylthio acid 3. Several chiral compounds including (-)-menthol, (-)-8-phenylmenthol and a camphor based oxazolidinone 8 reacted with 3 to give α-phenylthio esters or amide. These sulfides cyclized efficiently when reacted with tributyltin hydride. Among the chiral auxiliaries used, 8-phenylmenthyl group displayed moderate asymmetric induction (64% ee for cis-product and 40% ee for trans-product). Based on this results, a transition state model was proposed to explain the observed stereoselectivity. In this model, due to π,π-orbital overlap of the phenyl ring and the carbonyl, the si-face of the most stable conformer of the radical was shielded. This controlled the carbon-carbon bond formation to occur from the re-face.
Stereogenic Reactions of the α-Carbon Radicals of 8-Phenylmenthyl Esters
Chen, Ming-Yi,Fang, Jim-Min,Tsai, Yeun-Min,Yeh, Ru-Long
, p. 1603 - 1604 (2007/10/02)
The stereoselective free-radical type reduction and cyclisation of 8-phenylmenthyl esters is described; the predominant products are considered to be derived from the transition states with conformations having the larger substituent anti to the alkoxy group of the ester.
