Journal of Organic Chemistry p. 5370 - 5376 (1993)
Update date:2022-08-11
Topics:
Galeotti, Nathalie
Poncet, Joeel
Chiche, Laurent
Jouin, Patrick
The reduction of (5S)-5-alkyl-2,4-dioxopyrrolidines, so-called tetramic acids, by NaBH4 gives only partial diastereofacial selectivity in the case of the N-substituted analogues 9f-i, unlike the carbamate derivatives 9a-e which give the reduced cis-pyrrolidinones 10βa-e.Increasing the steric hindrance of either the N- or C-5-substituents enhances the re-face selectivity.On the other hand, reduction of the heterobicyclic compound 9n leads to a dramatic reversal of the stereoselectivity.Preliminary calculations show that the N-atom of the ring is slightlypyramidalized; the direction of hydride addition could be a consequence of this finding.
View MoreContact:86-310-8067016
Address:East Fuhua Road,Tiexi Chemical Industrial Estate,Hebei,China
Contact:+86-0592 5353131
Address:No.56 Guani Road Software Park 2,Siming District
Chongqing maohuan Chemicals Co., Ltd
website:http://www.bschem.com
Contact:+86 13996103726
Address:Chongqing Nan'an District Tu Town
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
JOY (TIANJIN) TECHNOLOGY AND DEVELOPMENT CO., LTD.
Contact:+86-22-66666666
Address:Tianjin
Doi:10.1080/14786410802265415
(2009)Doi:10.1002/cctc.201901443
(2020)Doi:10.1021/j100402a039
(1986)Doi:10.1039/b408386p
(2004)Doi:10.1016/S0040-4039(01)84469-5
(1972)Doi:10.1039/b907109a
(2009)