Synthesis of 3 or 3,3′-substituted BINOL ligands and their application in the asymmetric addition of diethylzinc to aromatic aldehydes

被引：29

作者：

Guo, QS ^{[1
]}

Liu, B ^{[1
]}

Lu, YN ^{[1
]}

Jiang, FY ^{[1
]}

Song, HB ^{[1
]}

Li, JS ^{[1
]}

机构：

[1] Nankai Univ, State Key Lab ElementoOrgan Chem, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 22期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetasy.2005.09.018

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Three new substituted BINOL ligands (R)-3-[4,6-bis(dimethylamino)-1,3,5-triazin-2-yl]-1,1'-bi-2-naphthol (R)-1, (R)3,3'-bis[4,6-bis(dimethylamino)-1,3,5 -triazin-2-yl]-1, 1'-bi-2-naphthol (R)-2 and 2,4-bis(2,2'-dihydroxy-1,1'-binaphthalen-3-yl)-6-(ptolyl)-1,3,5-triazine (R,R)-3 have been obtained by directed ortho-lithiation or Suzuki cross-coupling process. Ligand (R)-1 shows improved catalytic properties for the asymmetric diethylzinc addition to aromatic aldehydes. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3667 / 3671

页数：5

共 50 条

[21] Synthesis chiral cis-3-hydroxyazetidines and their application in diethylzinc addition to aldehydes
Zhang, Zhanbin
Li, Min
Zi, Guofu
CHIRALITY, 2007, 19 (10) : 802 - 808
[22] The synthesis of silica-supported chiral BINOL: Application in Ti-catalyzed asymmetric addition of diethylzinc to aldehydes
Pathak, Kavita
Ahmad, Irshad
Abdi, Sayed H. R.
Kureshy, Rukhsana I.
Khan, Noor-ul H.
Jasra, Raksh V.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2008, 280 (1-2) : 106 - 114
[23] 3,3′-Functionalized octahydro-BINOL:: a facile synthesis and its high enantioselectivity in the alkyne addition to aldehydes
Liu, L
Pu, L
TETRAHEDRON, 2004, 60 (34) : 7427 - 7430
[24] Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(BINOL) complex
Tetrahedron Asymmetry, 4 (585):
[25] The synthesis of dendritic BINOL ligands and their applications in the enantioselective Lewis acid catalyzed addition of diethylzinc to aldehydes
Fan, QH
Liu, GH
Chen, XM
Deng, GJ
Chan, ASC
TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1559 - 1565
[26] Titanium(IV) as an essential promoter in the asymmetric addition of diethylzinc to aldehydes catalyzed by aminonaphthol and imme ligands based on 3-substituted binaphthol
Jiang, Fu-Yong
Liu, Bing
Dong, Zhi-Bing
Li, Jin-Shan
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (20) : 4377 - 4380
[27] Chemoselective functionalization of 3,3′-substituted BINOL derivatives
Coluccini, Carmine
Castelluccio, Antonio
Pasini, Dario
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (11): : 4237 - 4240
[28] Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes
Zhang, Xun
Yang, Nianfa
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (04) : 1027 - 1032
[29] Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes
Dean, Melissa A.
Hitchcock, Shawn R.
TETRAHEDRON-ASYMMETRY, 2010, 21 (20) : 2471 - 2478
[30] Synthesis of N-α-pyridylmethyl amino alcohols and application in catalytic asymmetric addition of diethylzinc to aromatic aldehydes
Wu, YJ
Yun, HY
Wu, YS
Ding, KL
Zhou, Y
TETRAHEDRON-ASYMMETRY, 2000, 11 (17) : 3543 - 3552

← 1 2 3 4 5 →