Synthesis of C3-symmetric tris(β-hydroxy amide) ligands and their Ti(IV) complex-catalyzed enantioselective alkynylation of aldehydes

被引：82

作者：

Fang, T ^{[1
]}

Du, DM ^{[1
]}

Lu, SF ^{[1
]}

Xu, JX ^{[1
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Coll Chem & Mol Engn, Beijing 100871, Peoples R China

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 11期

关键词：

D O I：

10.1021/ol050047v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new chiral C-3-symmetric tris(beta-hydroxy amide) ligands have been synthesized via the reaction of 1,3,5-benzenetricarboxylic chloride and optically pure amino alcohols (up to 96% yield). The asymmetric catalytic alkynylation of aldehydes with these new C3-symmetric chiral tris(beta-hydroxy amide) ligands and Ti ((OPr)-Pr-/)4 Was investigated. Ligand 4c synthesized from (1R,2S)-(-)-2-amino-1,2-diphenylethanol is effective for the enantioselective alkynylation of various aldehydes, and high enantioselectivity was obtained with aromatic aldehydes and alpha,beta-unsaturated aldehyde (up to 92% ee).

引用

页码：2081 / 2084

页数：4

共 58 条

[1] A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) : 9687 - 9688
[2] Bellemin-Laponnaz S, 2002, ANGEW CHEM INT EDIT, V41, P3473, DOI 10.1002/1521-3773(20020916)41:18<3473::AID-ANIE3473>3.0.CO
[3] 2-N
[4] Stereoselective syntheses of epothilones A and B via directed nitrile oxide cycloaddition
Bode, JW
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) : 3611 - 3612
[5] Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions
Boyall, D
Frantz, DE
Carreira, EM
[J]. ORGANIC LETTERS, 2002, 4 (15) : 2605 - 2606
[6] Enantioselective addition of 2-methyl-3-butyn-2-ol to aldehydes:: Preparation of 3-hydroxy-1-butynes
Boyall, D
López, F
Sasaki, H
Frantz, D
Carreira, EM
[J]. ORGANIC LETTERS, 2000, 2 (26) : 4233 - 4236
[7] Facile and practical enantioselective synthesis of propargylic alcohols by direct addition of alkynes to aldehydes catalyzed by chiral disulfide-oxazolidine ligands
Braga, AL
Appelt, HR
Silveira, CC
Wessjohann, LA
Schneider, PH
[J]. TETRAHEDRON, 2002, 58 (52) : 10413 - 10416
[8] Novel concepts in directed biaryl synthesis.: Part 107.: Synthesis of enantiopure axially chiral C3-symmetric tripodal ligands and their application as catalysts in the asymmetric addition of dialkylzinc to aldehydes
Bringmann, G
Pfeifer, RM
Rummey, C
Hartner, K
Breuning, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) : 6859 - 6863
[9] Burk M. J., 1990, ANGEW CHEM, V102, P1511
[10] NEW CHIRAL PHOSPHOLANES - SYNTHESIS, CHARACTERIZATION, AND USE IN ASYMMETRIC HYDROGENATION REACTIONS
BURK, MJ
FEASTER, JE
HARLOW, RL
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (07) : 569 - 592

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