Organic and Biomolecular Chemistry p. 2062 - 2070 (2014)
Update date:2022-09-26
Topics:
Yazerski, Vital A.
Spannring, Peter
Gatineau, David
Woerde, Charlotte H.M.
Wieclawska, Sara M.
Lutz, Martin
Kleijn, Henk
Klein Gebbink, Robertus J.M.
The limited availability of catalytic reaction components may represent a major hurdle for the practical application of many catalytic procedures in organic synthesis. In this work, we demonstrate that the mixture of isomeric iron complexes [Fe(OTf)2(mix-BPBP)] (mix-1), composed of Λ-α-[Fe(OTf)2(S,S-BPBP)] (S,S-1), Δ-α- [Fe(OTf)2(R,R-BPBP)] (R,R-1) and Δ/Λ-β-[Fe(OTf) 2(R,S-BPBP)] (R,S-1), is a practical catalyst for the preparative oxidation of various aliphatic compounds including model hydrocarbons and optically pure natural products using hydrogen peroxide as an oxidant. Among the species present in mix-1, S,S-1 and R,R-1 are catalytically active, act independently and represent ca. 75% of mix-1. The remaining 25% of mix-1 is represented by mesomeric R,S-1 which nominally plays a spectator role in both C-H and C=C bond oxidation reactions. Overall, this mixture of iron complexes displays the same catalytic profile as its enantiopure components that have been previously used separately in sp3 C-H oxidations. In contrast to them, mix-1 is readily available on a multi-gram scale via two high yielding steps from crude dl/meso-2,2′-bipyrrolidine. Next to its use in C-H oxidation, mix-1 is active in chemospecific epoxidation reactions, which has allowed us to develop a practical catalytic protocol for the synthesis of epoxides.
View MoreLiaoning Yufeng Chemical Co.,Ltd.
Contact:86-0419-3418888
Address:The metallurgical industrial zone,shoushan town, Liaoyang, Liaoning, China
SHAANXI TOP PHARM CHEMICAL CO.LTD
Contact:+86-029-85733403
Address:No.108 ,west sector,south er huan,xi'an,china
Changzhou naidechemical Co.Ltd
Contact:+86-519-82589807
Address:NO.25,Houyang street,Jintan,Changzhou City
Anhui Sunsing Chemicals Co.,Ltd
website:http://www.sunsingchem.com
Contact:0086-566-2023179
Address:Jin An industry park, Chizhou economic technical development zone, Anhui
Contact:86 21 3772 9386
Address:Rm.1803,Starry Bldg.1,1505 Meijiabang Road,Shanghai 201620 China
Doi:10.1016/0040-4039(91)80502-W
(1991)Doi:10.1007/BF00480884
(1990)Doi:10.1016/S0040-4039(00)97985-1
(1990)Doi:10.1080/14756366.2019.1571272
(2019)Doi:10.1080/00397911.2010.516860
(2011)Doi:10.1081/SCC-120002519
(2002)