@article{oai:kanagawa-u.repo.nii.ac.jp:00012916,
 author = {加部, 義夫},
 journal = {Science Journal of Kanagawa University},
 month = {Jun},
 note = {Organic compounds containing carbon-metal bonds are called organometallic compounds. Such compounds have been known and studied since the 19th century and have been widely applied to influerce. synthetic transformation in modern organic chemistry. Many educational benefits could result from the use of reaction types and discovery episodes for undergraduates and graduate classes in organic and organometallic chemistry. Wilke, the successor of Ziegler and director of Max-Planck-Institute für Kohlenforschung, took over research on the Ni-effect, which brought about the discovery of the Ziegler-Natta catalyst. He discovered the TiCl4/AlEt2Cl catalyzed oligomerization reaction of butadiene to yield cyclododecatriene (CDT) without a olymer. Furthermore, the olefin and π-allyl Ni-complexes were isolated and found to act as important intermediates for oligomerization. Around the same time, the Wacker method was applied to industrial reactions in which water was added to ethylene ligand of the Pd(II) complex to give acetoaldehyde. Tsuji discovered a similar type of reaction : nucleophile addition to the π-allyl ligand of the π-ally Pd (II) complex, which was developed to Pd(0) catalyzed allylation (Tsuji –Trost reaction). On the other hand the heterogeneous Ni catalyst has been applied to the industrial hydrogenation reaction since its discovery by Sabatier. When Wilkinson modified Rh(III) (Pyridine)3Cl3 as one of the homogeneous hydrogenation catalysts with Ph3P instead of pyridine as a ligand, he serendipitously discovered the very active and coordinatively unsaturated Rh(I)(Ph3P)3Cl complex (Wilkinson catalyst). Knowles and the Monsant company applied these phosphine Rh(I) catalysts to the asymmnetric synthesis of amino acid derivatives such as L-doapa. After that, Kagen and Noyori improved phosphine ligands such as DIPHOS and BIANP, which resulted in high optical yield syntheses of amino acids from 83 to 100% enantiomer excess (ee), respectively., Departmental Bulletin Paper, 教育論文},
 pages = {111--118},
 title = {反応のタイプと発見のエピソードで学ぶ有機金属化学(6)},
 volume = {30},
 year = {2019}
}