76530-00-2Relevant academic research and scientific papers
Synthesis of Rhodium Complexes with Chiral Diene Ligands via Diastereoselective Coordination and Their Application in the Asymmetric Insertion of Diazo Compounds into E?H Bonds
Ankudinov, Nikita M.,Chusov, Denis A.,Nelyubina, Yulia V.,Perekalin, Dmitry S.
, p. 18712 - 18720 (2021/07/20)
A new method for the synthesis of chiral diene rhodium catalysts is introduced. The readily available racemic tetrafluorobenzobarrelene complexes [(R2-TFB)RhCl]2 were separated into two enantiomers via selective coordination of one of them with the auxiliary S-salicyl-oxazoline ligand. One of the resulting chiral complexes with an exceptionally bulky diene ligand [(R,R-iPr2-TFB)RhCl]2 was an efficient catalyst for the asymmetric insertion of diazoesters into B?H and Si?H bonds giving the functionalized organoboranes and silanes with high yields (79–97 %) and enantiomeric purity (87–98 % ee). The stereoselectivity of separation via auxiliary ligand and that of the catalytic reaction was predicted by DFT calculations.
Erratum: Oxazaborolidinium Ion-Catalyzed Cyclopropanation of α-Substituted Acroleins: Enantioselective Synthesis of Cyclopropanes Bearing Two Chiral Quaternary Centers (J. Am. Chem. Soc. (2011) 133:51 (20708?20711) DOI: 10.1021/ja209270e)
Gao, Lizhu,Hwang, Geum-Sook,Ryu, Do Hyun
supporting information, p. 6021 - 6022 (2021/05/13)
Pages 20709 and 20710. In the published version of the paper, the trans:cis ratios of 2w and 2x were reversed. The revised results were confirmed by NOE experiments and comparison of the optical rotation data with reported values after transformation. The
Oxazaborolidinium ion-catalyzed cyclopropanation of α-substituted acroleins: Enantioselective synthesis of cyclopropanes bearing two chiral quaternary centers
Gao, Lizhu,Hwang, Geum-Sook,Ryu, Do Hyun
supporting information; experimental part, p. 20708 - 20711 (2012/02/06)
A catalytic synthetic route to highly functionalized chiral cyclopropane derivatives was developed by Michael-initiated cyclopropanation of α-substituted acroleins with aryl- and alkyl diazoacetates. In the presence of chiral (S)-oxazaborolidinium cation
Construction of stereodefined 1,1,2,2-tetrasubstituted cyclopropanes by acid catalyzed reaction of aryldiazoacetates and α-substituted acroleins
Hashimoto, Takuya,Naganawa, Yuki,Kano, Taichi,Maruoka, Keiji
, p. 5143 - 5145 (2008/09/19)
Michael-initiated ring closure of aryldiazoacetates and α-substituted acroleins under acid catalysis offers a unique opportunity for the stereoselective formation of various tetrasubstituted cyclopropanes. The Royal Society of Chemistry.
