Asymmetric 1,3-dipolar cycloaddition reaction between α,β-unsaturated aldehydes and nitrones catalyzed by well-defined iridium or rhodium catalysts

被引：37

作者：

Carmona, Daniel ^{[1
]}

Lamata, M. Pilar ^{[1
]}

Viguri, Fernando ^{[1
]}

Rodriguez, Ricardo ^{[1
]}

Fischer, Thomas ^{[1
]}

Lahoz, Fernando J. ^{[1
]}

Dobrinovitch, Isabel T. ^{[1
]}

Oro, Luis A. ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Inst Univ Catalisis Homogenea,Dept Quim Inorgan, E-50009 Zaragoza, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 10期

关键词：

asymmetric catalysis; 1,3-dipolar cycloaddition reactions; enals; iridium; nitrones; rhodium;

D O I：

10.1002/adsc.200700010

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Reaction of the complexes (S-M,R-C)-[(eta(5)-C5Me5)M{(R)-Prophos}(H2O)](SbF6)(2) (M=Rh, Ir) with alpha,beta-unsaturated aldehydes diastereoselectively gave complexes (S-M,R-C)-[(eta(5)-C5Me5)M{(R)-Prophos}(enal)](SbF6)(2) which have been fully characterized, including an X-ray molecular structure determination of the complex (S-Rh,R-C)- [(eta(5)-C5Me5)Rh{(R)-Prophos)(trans-2-methyl-2-pentenal)](SbF6)(2). These enal complexes efficiently catalyze the enantioselective 1,3-dipolar cycloaddition of the nitrones N-benzylideneaniline N-oxide and 3,4-dihydroisoquinoline N-oxide to the corresponding enals. Reactions occur with excellent regioselectivity, perfect endo selectivity and with enantiomeric excesses up to 94%. The absolute configuration of the adduct 5-methyl-2,3-diphenylisoxazolidine-4-carboxaldehyde was determined through its (R)-(-)-alpha-methylbenzylamine derivative.

引用

页码：1751 / 1758

页数：8

共 50 条

[31] Enantio- and Diastereoselective Synthesis of Isoxazolidines by Asymmetric 1,3-Dipolar Cycloaddition of Nitrones
Ukaji, Y.
Taniguchi, K.
Sada, K.
Inomata, K.
Chemistry Letters, (06):
[32] Metal-catalyzed asymmetric 1,3-dipolar cycloaddition reactions
Gothelf, KV
Jorgensen, KA
ACTA CHEMICA SCANDINAVICA, 1996, 50 (08): : 652 - 660
[33] Endo-selective asymmetric inverse electron-demand 1,3-dipolar cycloaddition reaction of nitrones
Ashizawa, Tomoko
Ohtsuki, Natsuki
Miura, Tomoyuki
Ohya, Makoto
Shinozaki, Takaomi
Ikeno, Taketo
Yamada, Tohru
HETEROCYCLES, 2006, 68 (09) : 1801 - 1810
[34] 1,3-Dipolar cycloaddition of isatinN,N′-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water
Wang, Zhan-Yong
Yang, Ting
Chen, Rongxiang
Ma, Xueji
Liu, Huan
Wang, Kai-Kai
RSC ADVANCES, 2020, 10 (41) : 24288 - 24292
[35] Iron- and ruthenium-Lewis acid catalyzed asymmetric 1,3-dipolar cycloaddition reactions between enals and diaryl nitrones
Badoiu, Andrei
Bernardinelli, Gerald
Mareda, Jiri
Kuendig, E. Peter
Viton, Florian
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1298 - 1311
[36] Catalytic Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with α,β-Unsaturated Ketones
Hernandez-Toribio, Jorge
Gomez Arrayas, Ramon
Martin-Matute, Belen
Carretero, Juan C.
ORGANIC LETTERS, 2009, 11 (02) : 393 - 396
[37] Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α,ß-Unsaturated Amide and Azomethine Imine
Li, Zhao
Kumagai, Naoya
Shibasaki, Masakatsu
CHEMICAL & PHARMACEUTICAL BULLETIN, 2020, 68 (06) : 552 - 554
[38] Synthesis of iminosugars via 1,3-dipolar cycloaddition reactions of nitrones to α,β-unsaturated sugar aldonolactones
Stecko, Sebastian
Jurczak, Margarita
Panfil, Irma
Furman, Bartlomiej
Grzeszczyk, Barbara
Chmielewski, Marek
COMPTES RENDUS CHIMIE, 2011, 14 (01) : 102 - 125
[39] SYNTHESIS OF 5-AMINOISOXAZOLIDINES BY 1,3-DIPOLAR CYCLOADDITION REACTION OF NITRONES WITH ENAMINES
NOMURA, Y
FURUSAKI, F
TAKEUCHI, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (09) : 3002 - +
[40] Synthesis of some new isoxazolidines by 1,3-dipolar cycloaddition reaction of nitrones and olefins
Mobinikhaledi, A
Foroughifar, N
Kalate, Z
TURKISH JOURNAL OF CHEMISTRY, 2005, 29 (02) : 147 - 152

← 1 2 3 4 5 →