Synthesis and resolution of racemic 2-amino-2'-hydroxy-1,1'-binaphthyl

被引：46

作者：

Smrcina, M ^{[1
]}

Vyskocil, S ^{[1
]}

Polivkova, J ^{[1
]}

Polakova, J ^{[1
]}

Kocovsky, P ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,LEICS,ENGLAND

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 1996年 / 61卷 / 10期

关键词：

binaphthyls; oxidative coupling; resolution;

D O I：

10.1135/cccc19961520

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The title compound 3 has been prepared via a highly selective, Cu(II)-mediated cross-coupling of 2-aminonaphthalene 1 and 2-naphthol 2 and resolved into enantiomers via crystallization of diastereoisomeric salts with (1S)-(+)-10-camphorsulfonic acid. The method has been optimized and the use of chromatography eliminated.

引用

页码：1520 / 1524

页数：5

共 50 条

[21] Transition-Metal-Free Direct Arylation: Synthesis of Halogenated 2-Amino-2′-hydroxy-1,1′-biaryls and Mechanism by DFT Calculations
Gao, Hongyin
Ess, Daniel H.
Yousufuddin, Muhammed
Kuerti, Laszlo
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (19) : 7086 - 7089
[22] Efficient synthesis of optically active 2-amino-2′-diphenylphosphino-1,1′-binaphthyl and its derivatives
Sumi, K
Ikariya, T
Noyori, R
CANADIAN JOURNAL OF CHEMISTRY, 2000, 78 (06) : 697 - 703
[23] THE REACTION OF BETA-NAPHTHOL, BETA-NAPHTHYLAMINE AND FORMALDEHYDE .1. 2-AMINO-2'-HYDROXY-1,1'-DINAPHTHYLMETHANE
CORLEY, RS
BLOUT, ER
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (04) : 755 - 760
[24] 2-Diphenylphosphino-2′-hydroxy-1,1′-binaphthyl as a chiral auxiliary for asymmetric coordination chemistry
Gong, Lei
Mueller, Christian
Celik, Mehmet Ali
Frenking, Gernot
Meggers, Eric
NEW JOURNAL OF CHEMISTRY, 2011, 35 (04) : 788 - 793
[25] Enantioselective Synthesis of 3,3′-Disubstituted 2-Amino-2′-hydroxy-1,1′-binaphthyls by Copper-Catalyzed Aerobic Oxidative Cross-Coupling
Zhao, Xiao-Jing
Li, Zi-Hao
Ding, Tong-Mei
Tian, Jin-Miao
Tu, Yong-Qiang
Wang, Ai-Fang
Xie, Yu-Yang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (13) : 7061 - 7065
[26] Synthesis and separation of the atropisomers of 2-(5-benzo[b]fluorenyl)-2′-hydroxy-1,1′-binaphthyl and related compounds
Yang, Hua
Petersen, Jeffrey L.
Wang, Kung K.
TETRAHEDRON, 2006, 62 (34) : 8133 - 8141
[27] SOLID STATE RESOLUTION OF RACEMIC 1,1'-BINAPHTHYL
PINCOCK, RE
WILSON, KR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (05) : 1291 - &
[28] Highly enantioselective additions of diethylzinc to aldehydes using 2-triflamido-methyl-2′-hydroxy-1,1′- binaphthyl
Kang, SW
Ko, DH
Kim, KH
Ha, DC
ORGANIC LETTERS, 2003, 5 (23) : 4517 - 4519
[29] Synthesis and crystallographic characterization of a chiral complex of (R)-2-(pyridin-2-ylmethylene)amino-2'-hydroxy-1,1'binaphthyl(L) with hydrated nickel(II) acetate
Ji, Baoming
Han, Xiangming
CRYSTAL RESEARCH AND TECHNOLOGY, 2007, 42 (09) : 926 - 929
[30] Dynamic Thermodynamic Resolution of Racemic 1,1′-Binaphthyl-2,2′-diol (BINOL)
Shaashua, Omer
Pollok, Dennis
Dyadyuk, Alina
Shames, Alexander I.
Waldvogel, Siegfried R.
Pappo, Doron
ORGANIC LETTERS, 2024, 26 (10) : 2129 - 2134

← 1 2 3 4 5 →