Tetrahedron p. 7855 - 7866 (1997)
Update date:2022-08-03
Topics:
Weigel, Wilfried
Schiller, Sabine
Henning, Hans-Georg
Irradiation of β-aminopropiophenones 1 leads to the formation of 2-aminocyclopropanols 2 which can undergo oxidative ring opening to give enaminones 3. The regioselectivity of cyclopropanol formation of the α-benzyl substituted 1 is determined by the preferred charge transfer interaction between the photoexcited benzoyl chromophore and the amino group. The photocyclizations of the α- or β-substituted 1 proceed stereoselectively. No photoracemization of the pure enantiomers of 1m, independent of the solvent polarity was observed. Aryl or alkyl substituents at the C(3)- or C(2)-ring atom stabilize the cyclopropanol derivatives. The formation of 3 indicates regioselective C(1)-C(2) ring opening of 2 probably by localization of the excitation energy.
View MoreContact:+86 21 34123252
Address:14, 4580 Dushi, Shanghai, China
Suzhou BEC Fine Chemicals Co., Ltd.
website:http://www.bek.com.cn
Contact:0512-68095917 18913193865
Address:6, Jin Shan Road, Suzhou New District, 215011 China Suzhou Nations Pharmaceutical Innovation Center Inside
Jintan City Mego Chemical Co., Ltd
Contact:+86-0519-82814387
Address:23# Dengguan Town, Jintan, Jiangsu Province, China
Shanghai Gsyn Chemical Co.,Ltd.
Contact:86-021-67158290
Address:86-021-67158291
Jiangxi Dongxu Chemical Science & Technology Co.,Ltd
Contact:+86-791-86899381
Address:Nanchang, Jiangxi, China
Doi:10.1055/s-1977-24461
(1977)Doi:10.1021/ja01532a070
()Doi:10.1055/s-0040-1707321
(2021)Doi:10.1039/a700300e
(1997)Doi:10.1016/0040-4039(96)01663-2
(1996)Doi:10.1016/S0277-5387(96)00541-4
(1997)