Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes

被引：5

作者：

Sweetman, Brian A. ^{[1
]}

Guiry, Patrick J. ^{[1
]}

机构：

[1] Univ Coll Dublin, Sch Chem, Ctr Synth & Chem Biol, Dublin 4, Ireland

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

关键词：

Axial chirality; Tridentate ligand; Asymmetric catalysis; Isoquinoline; Chiral alcohol; ATROPISOMERIC PHOSPHINAMINE LIGAND; BIS(OXAZOLINE) LIGANDS; ENANTIOSELECTIVE ADDITION; ALDOL ADDITIONS; RESOLUTION; COMPLEXATION; QUINAZOLINE; RECOGNITION; ALLYLATION; CHLORIDE;

D O I：

10.1016/j.tet.2018.07.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and resolution of new tridentate isoquinoline-derived ligands has been developed. The key steps in the synthetic sequence include successive, chemo-selective Suzuki-Miyaura cross-couplings of 1,3-dichloroisoquinoline with suitable arylboronic acids. The new ligands prepared in this manner were resolved either via molecular complexation with N-benzylcinchonidinium chloride as with 1-[3-(2-hydroxyphenyl)isoquinolin-1-yl]naphthalen-2-ol or via chromatographic separation of its epimeric camphorsulfonates as for 1,3-bis-(2-hydroxynaphthalen-1-yl)isoquinoline. 4-tert-Butyl-2-chloro-6-[1-(2-hydroxymethylnaphthalen-1-yl)isoquinolin-3-yliphenol was resolved by chiral semi-preparative HPLC. The application of these ligands in the diethylzinc addition to aldehydes was investigated. In certain cases, the desired secondary alcohols were obtained in high yield with excellent enantiomeric excess (ee > 99%) at low catalyst loading (1 mol%). (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5567 / 5581

页数：15

共 50 条

[11] The enantioselective addition of diethylzinc to aldehydes catalyzed by 2-methylquinoline derived chiral ligands
Xu, QY
Wang, GX
Pan, XF
[J]. CHINESE CHEMICAL LETTERS, 2001, 12 (05) : 395 - 396
[12] New indane derived aminoalcohols as chiral ligands for the catalytic enantioselective addition of diethylzinc to aldehydes
Sola, L
VidalFerran, A
Moyano, A
Pericas, MA
Riera, A
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (10) : 1559 - 1568
[13] Enantioselective addition of diethylzinc to aldehydes in the presence of chiral aprotic ligands
Jin, MJ
Kim, YM
Lee, KS
[J]. TETRAHEDRON LETTERS, 2005, 46 (15) : 2695 - 2696
[14] Modular Prolinol Chiral Ligands for Enantioselective Addition of Diethylzinc to Aromatic Aldehydes
Gou, Shaohua
Ye, Zhongbin
Feng, Mingming
Jiang, Wenchao
[J]. SYNTHETIC COMMUNICATIONS, 2013, 43 (07) : 941 - 950
[15] Enantioselective addition of diethylzinc to aldehydes in the presence of chiral hydrazone and imine ligands
Mino, Takashi
Suzuki, Atsushi
Yamashita, Masakazu
Narita, Shusaku
Shirae, Yoshiaki
Sakamoto, Masami
Fujita, Tsutomu
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (20) : 4297 - 4303
[16] Synthesis and application of oxadiazines as chiral ligands for the enantioselective addition of diethylzinc to aldehydes
Dean, Melissa A.
Hitchcock, Shawn R.
[J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (20) : 2471 - 2478
[17] New chiral Schiff base as a tridentate ligand for catalytic enantioselective addition of diethylzinc to aldehydes
Tanaka, Takanori
Yasuda, Yorinobu
Hayashi, Masahiko
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18): : 7091 - 7093
[18] L-Proline-Derived Tertiary Amino Alcohols as Chiral Ligands for Enantioselective Addition of Diethylzinc to Aldehydes
Xu, Zhou
Bo, Rongcheng
Wu, Nan
Wan, Yu
Wu, Hui
[J]. LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (08) : 582 - 586
[19] Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes
Lu, J
Xu, XN
Wang, C
He, HG
Hu, YF
Hu, HW
[J]. TETRAHEDRON LETTERS, 2002, 43 (46) : 8367 - 8369
[20] Vasicine as tridentate ligand for enantioselective addition of diethylzinc to aldehydes
Aga, Mushtaq A.
Kumar, Brijesh
Rouf, Abdul
Shah, Bhahwal A.
Taneja, Subhash C.
[J]. TETRAHEDRON LETTERS, 2014, 55 (16) : 2639 - 2641

← 1 2 3 4 5 →