Improved one-pot synthesis of styryl tetrahydrofurans and cyclohexanes by radical addition to beta-nitrostyrenes in the presence of benzoyl peroxide.
Stereoselective styryl derivatives have been prepared based on radical substitution (addition-elimination) of heterocycles or cyclohydrocarbons units to (E)-beta-nitrostyrenes 1 using a common radical initiator benzoyl peroxide. High reactivity and selectivity with wide substrate scope were attained by using this easy methodology. The reactions using easily obtained and one-pot potential starting materials gave excellent trans-selectivity with medium to high yields in all cases. Synthetic utility of this approach has been demonstrated by the preparation of various trans-styryl derivatives.
Jang
Yeong-Jiunn
YJ
Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei, 116 Taiwan, Republic of China.
Shih
Yuh-Kuo
YK
Liu
Jing-Yuan
JY
Kuo
Wen-Yu
WY
Yao
Ching-Fa
CF
D001585:Benzoyl Peroxide / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D005609:Free Radicals; D005663:Furans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013343:Styrenes / Q000138:chemical synthesis*
D003510:Cyclohexanes; D005609:Free Radicals; D005663:Furans; D013343:Styrenes; C011955:beta-nitrostyrene; D001585:Benzoyl Peroxide