Enantioselective Addition of Phenylacetylene to Aldehydes Catalyzed by Polymer-Supported Titanium(IV) Complexes of β-Hydroxy Amides

被引：5

作者：

Hui, Xin-Ping ^{[1
]}

Huang, Lu-Ning ^{[1
]}

Li, Ya-Min ^{[1
]}

Wang, Ren-Lin ^{[1
]}

Xu, Peng-Fei ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Peoples R China

来源：

CHIRALITY | 2010年 / 22卷 / 03期

基金：

中国国家自然科学基金;

关键词：

enantioselective addition; polymer-supported catalyst; titanium tetraisopropoxide; diethylzinc; beta-hydroxy amide; ASYMMETRIC TRANSFER HYDROGENATION; ENANTIO-SELECTIVE ADDITION; AROMATIC-ALDEHYDES; TERMINAL ALKYNES; RECOVERABLE CATALYSTS; PROPARGYLIC ALCOHOLS; ALDOL REACTION; LIGANDS; ALKYNYLATION; KETONES;

D O I：

10.1002/chir.20749

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of polymer-supported chiral beta-hydroxy amides and C(z)-symmetric beta-hydroxy amides have been synthesized and successfully used for the enantioselective addition of phenylacetylene to aldehydes. High yields (up to 93%) and enantioselectivities (up to 92% ee) were achieved by using polymer-supported chiral hydroxy amide 4b. The resin 4b is reused four times, giving the product with enantioselectivity 80% ee. Fortunately, it is found that this heterogonous system is suitable not only for aromatic aldehydes but also aliphatic aldehyde. Chirality 22:347-354, 2010. (C) 2009 Wiley-Liss, Inc.

引用

页码：347 / 354

页数：8

共 36 条

[31] 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
[32] Enantioselective Diethylzinc Addition to Aromatic Aldehydes Catalyzed by Novel Ti(IV) Complex of Three-Dentate Chiral Sulfonamide Ligands
Dabiri, Minoo
Salehi, Peyman
Heydari, Seddigheh
Kozehgary, Gholamreza
SYNTHETIC COMMUNICATIONS, 2009, 39 (24) : 4350 - 4361
[33] Facile synthesis of C3-symmetric tripodal β-hydroxy amide ligands and their Ti (IV) complex-catalyzed asymmetric addition of diethylzinc to aldehydes
Fang, Tao
Xu, Jiaxi
Du, Da-Ming
LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (10) : 780 - 786
[34] Asymmetric addition of diethylzinc to benzaldehyde catalyzed by novel chiral C2-symmetric tetrakis(sulfonamide)-titanium(IV) complexes
Venegas, Antonio
Rivas, Lucrecia
Huelgas, Gabriela
Anaya de Parrodi, Cecilia
Madrigal, Domingo
Aguirre, Gerardo
Parra-Hake, Miguel
Chavez, Daniel
Somanathan, Ratnasamy
TETRAHEDRON-ASYMMETRY, 2010, 21 (24) : 2944 - 2948
[35] Asymmetric Addition of Pyridyl Aluminum Reagents to Aldehydes Catalyzed by a Titanium(IV) Catalytic System of (R)-H8-BINOLate
Zhang, Lijun
Tu, Bing
Ge, Min
Li, Yimei
Chen, Liangyu
Wang, Wei
Zhou, Shuangliu
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16) : 8307 - 8313
[36] Polymer-Supported Highly Enantioselective Catalyst for Nitro-Michael Addition: Tuning through Variation of the Number of H-Bond Donors and Spacer Length
Tuchman-Shukron, Lital
Portnoy, Moshe
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (04) : 541 - 546

← 1 2 3 4 →