59239-89-3Relevant academic research and scientific papers
Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P,C-stereogenic centers
Yang, Meng,Xu, Hao,Zhou, Zhong-Yang,Zhang, He,Liu, Li-Juan,Sun, Yong-Ming,Nie, Shao-Zhen,Zhao, Chang-Qiu
supporting information, p. 815 - 822 (2016/09/02)
α-Amino phosphinates with P,C-stereogenic centers were prepared from a P-retained addition of (RP)-(?)-menthyl H-phenylphosphinate to (R)-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single
O-Naphthoquinone-Catalyzed Aerobic Oxidation of Amines to (Ket)imines: A Modular Catalyst Approach
Goriya, Yogesh,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 5174 - 5177 (2016/10/14)
A modular aerobic oxidation of amines to imines has been achieved using an ortho-naphthoquinone (o-NQ) catalyst. The cooperative catalyst system of o-NQ and Cu(OAc)2 enabled the formation of homocoupled imines from benzylamines, while the presence of TFA helped the formation of cross-coupled imines in excellent yields. The current mild aerobic oxidation protocol could also be applied to the oxidation of secondary amines to imines or ketimines with the help of cocatalyst, Ag2CO3, with excellent yields.
Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines
Huang, Li,Zhang, Yu,Staples, Richard J.,Huang, Rui H.,Wulff, William D.
supporting information; experimental part, p. 5302 - 5313 (2012/05/20)
The catalytic asymmetric aziridination of imines and diazo compounds (AZ reaction) mediated by boroxinate catalysts derived from the VANOL and VAPOL ligands was investigated with chiral imines derived from five different chiral, disubstituted, methyl amines. The strongest matched and mismatched reactions with the two enantiomers of the catalyst were noted with disubstituted methyl amines that had one aromatic and one aliphatic substituent. The synthetic scope for the AZ reaction was examined in detail for α-methylbenzyl amine for cis-aziridines from α-diazo esters and for trans-aziridines from α-diazo acetamides. Optically pure aziridines could be routinely obtained in good yields and with high diastereoselectivity and the minor diastereomer (if any) could be easily separated. The matched case for cis-aziridines involved the (R)-amine with the (S)-ligand, but curiously, for trans-aziridines the matched case involved the (R)-amine with the (R)-ligand for imines derived from benzaldehyde and n-butanal, and the (R)-amine with the (S)-ligand for imines derived from the bulkier aliphatic aldehydes pivaldehyde and cyclohexane carboxaldehyde.
Further Studies of the Kinetic Template Effect in the Metal Ion-catalysed Reactions of ortho-Donor-substituted Aryl Halides with Tertiary Phosphines. Structural Requirements of the Template
Allen, David W.,Cropper, Paul E.,Smithurst, Peter G.,Ashton, Peter R.,Taylor, Brian F.
, p. 1989 - 1994 (2007/10/02)
The reactions of a series of Schiff's bases, derived from ortho-chloro-, bromo- or iodo-benzaldehydes and p-anisidine, with tertiary phosphines in the presence of nickel(II) bromide in refluxing ethanol proceed with displacement of the ortho-halogen to form the related ortho-substituted arylphosphonium salts.These reactions appear to be examples of a kinetic template effect in which the Schiff's base moiety aids the catalytic role of the metal ion in promoting the substitution reaction.Introduction of a second donor atom into the substituent group present at the nitrogen of related Schiff's bases inhibits the reactions due to diversion of the metal ion in other modes of coordination.The reactions are also inhibited by steric crowding at the imino-nitrogen.A range of other aryl halides bearing ortho-substituents having the potential to act as co-ordination templates has been prepared and their reactions with phosphines in the presence of metal ions studied enabling the rather critical nature of effective template groups to be defined.Detailed 13C n.m.r. data are also reported for the Schiff's bases and related arylphosphonium salts.
