Asymmetric Henry Reaction Using Cobalt Complexes with Bisoxazoline Ligands Bearing Two Fluorous Tags

被引:2
作者
Ishihara, Kazuki [1 ]
Kato, Yamato [1 ]
Takeuchi, Narisa [1 ]
Hayashi, Yuka [1 ]
Hagiwara, Yuna [1 ]
Shibuya, Shyota [1 ]
Natsume, Tohya [1 ]
Matsugi, Masato [1 ]
机构
[1] Meijo Univ, Fac Agr, 1-501 Shiogamaguchi,Tempaku Ku, Nagoya 4688502, Japan
关键词
fluorous; ligand; oxazoline; Henry reaction; absolute configuration; BIS(OXAZOLINE) LIGANDS; CATALYSTS; CYCLOPROPANATION; ALDOL;
D O I
10.3390/molecules28227632
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The effect of the presence of fluorous tags in bisoxazoline ligands on the stereoselectivity of the cobalt-catalyzed asymmetric Henry reaction was investigated. In contrast to the stereoselectivity obtained with conventional nonfluorous ligands, using bisoxazoline bidentate ligands featuring two fluorous tags in adjacent positions on the aromatic ring yielded a reversed stereoselectivity. The stereoselectivity also reversed when the fluorous tags were replaced with alkyl chains of equivalent length, albeit to a considerably lesser degree, highlighting the effect of the fluorous tags.
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页数:16
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共 36 条
[1]   Asymmetric Henry Reaction of Nitromethane with Substituted Aldehydes Catalyzed by Novel In Situ Generated Chiral Bis(β-Amino Alcohol-Cu(OAc)2•H2O Complex [J].
Alammari, Abdullah Saleh ;
Al-Majid, Abdullah Mohammed ;
Barakat, Assem ;
Alshahrani, Saeed ;
Ali, Mohammad ;
Islam, Mohammad Shahidul .
CATALYSTS, 2021, 11 (10)
[2]   Organocatalytic Enantioselective Henry Reactions [J].
Alvarez-Casao, Yolanda ;
Marques-Lopez, Eugenia ;
Herrera, Raquel P. .
SYMMETRY-BASEL, 2011, 3 (02) :220-245
[3]   Fluorous chiral bisoxazolines. Synthesis and applications to an asymmetric allylic alkylation [J].
Bayardon, J ;
Sinou, D .
TETRAHEDRON LETTERS, 2003, 44 (07) :1449-1451
[4]   Asymmetric cyclopropanation catalyzed by fluorous bis(oxazolines)-copper complexes [J].
Bayardon, Jerome ;
Holczknecht, Orsolya ;
Pozzi, Gianluca ;
Sinou, Denis .
TETRAHEDRON-ASYMMETRY, 2006, 17 (10) :1568-1572
[5]   DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].
COREY, EJ ;
IMAI, N ;
ZHANG, HY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729
[6]   Fluorous chiral bis(oxazolines): Synthesis and application in asymmetric Henry reaction [J].
Deng, Tao ;
Cai, Chun .
JOURNAL OF FLUORINE CHEMISTRY, 2013, 156 :183-186
[7]   BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].
EVANS, DA ;
WOERPEL, KA ;
HINMAN, MM ;
FAUL, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728
[8]   A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].
Evans, DA ;
Seidel, D ;
Rueping, M ;
Lam, HW ;
Shaw, JT ;
Downey, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693
[9]   C-2-symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters [J].
Evans, DA ;
MacMillan, DWC ;
Campos, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10859-10860
[10]   Recent advances in the immobilization of chiral catalysts containing bis(oxazolines) and related ligands [J].
Fraile, Jose M. ;
Garcia, Jose I. ;
Mayoral, Jose A. .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :624-646