Journal of Organic Chemistry p. 629 - 635 (1986)
Update date:2022-08-04
Topics:
Takaya, Hidemasa
Mashima, Kazushi
Koyano, Kinko
Practical methods for the synthesis of (R)- or (S)-2,2'bis(diarylphosphino)-1,1'-binaphthyls (BINAPs), useful ligands for transition-metal-catalyzed asymmetric reactions, have been developed. (+/-)-2,2'-Bis(diphenylphosphinyl)1,1'-binaphthyl <(+/-)-BINAPO>, prepared from 2,2'-dibromo-1,1'-binaphthyl and diphenylphosphinyl chloride, can be resolved into optical antipodes by the use of camphorsulfonic acid or 2,3-di-O-benzoyltartaric acid.Reduction of resolved BINAPO with trichlorosilane in the presence of triethylamine affords optically pure 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP).In a similar manner, several BINAP analogues have been prepared in optically pure form.The present procedures are suitable for obtaining these axially dissymmetric diphosphines in a large scale.The molecular structure of the 1:1:1 complex of (S)-(-)-BINAPO, (1R)-(-)-camphorsulfonic acid, and acetic acid has been studied by single-crystal X-ray analysis.
View MoreBeijing Harmony Chemical Co., Ltd.
Contact:86-010-84956928
Address:Room 207, Jin feng he B building, No 8 Xin Jie Kou Wai Street, Xi Cheng District, Beijing,PRC. 10008
Chengdu ZY Biochemical Technology Co., LTD
Contact:0086-28-88680086
Address:170 Qingpu Road, Shouan Town, Pujiang County
ABA Chemicals (Shanghai) Limited
Contact:021- 5115 9199-232
Address:Suite 18D, #201 Ningxia Road,
Changzhou LanXu Chemical Co.,ltd.(expird)
Contact:86-0519-86330911,13656129734,15261186386
Address:Room 524, Depart.Chemical, Changzhou Science and Eductaion town, Jiangsu, China;Factory: Haian Fine Chemical Industry Park,Nantong,Jiangsu,China
Beijing Hope Pharmaceutical Co., Ltd.
Contact:86-10-67886402
Address:309,Block 1 District B,No.12 Hongda North Road , Beijing Economic-Technological Development Area, Beijing, China
Doi:10.1021/ja01110a503
(1953)Doi:10.1021/acs.joc.7b02030
(2017)Doi:10.1016/j.tet.2007.11.016
(2008)Doi:10.1021/jm7012166
(2008)Doi:10.3987/COM-04-10216
(2005)Doi:10.1246/bcsj.58.1991
(1985)