A general, Bronsted acid-catalyzed hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles

被引：204

作者：

Wabnitz, TC ^{[1
]}

Spencer, JB ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 12期

关键词：

D O I：

10.1021/ol034596h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Strong Bronsted acids such as bis(trifluoromethariesulfon)imide catalyze the hetero-Michael addition of carbamates, alcohols, and thiols to alpha,beta-unsaturated ketones, alkylidene malonates, and acrylimides. Scope, reaction rates, and yields are superior to comparable Lewis acid-catalyzed processes.

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页码：2141 / 2144

页数：4

相关论文

共 61 条

[1]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[2]

2-E

[3] Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel [J].

Bartoli, G ;

Bosco, M ;

Marcantoni, E ;

Petrini, M ;

Sambri, L ;

Torregiani, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9052-9055

[4]

Berkessel A., 1995, METHODS ORGANIC CH E, VE21, P4818

[5] Intramolecular conjugate addition reactions of amines and carbamates to 2,5-cyclohexadien-1-ones: Stereoselective synthesis of perhydroindoles [J].

Bland, D ;

Chambournier, G ;

Dragan, V ;

Hart, DJ .

TETRAHEDRON, 1999, 55 (29) :8953-8966

[6] Synthesis of aziridine-2,2-dicarboxylates via 1,4-addition of N,O-(bistrimethylsilyl)hydroxylamine to α,β-unsaturated malonates [J].

Cardillo, G ;

Gentilucci, L ;

Gianotti, M ;

Perciaccante, R ;

Tolomelli, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8657-8660

[7] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[8]

Cossy J, 2002, SYNLETT, P45

[9] AN APPROACH TO THE SYNTHESIS OF BRUCEANTIN - THE SYNTHESIS OF A TETRACYCLIC INTERMEDIATE [J].

DARVESH, S ;

GRANT, AS ;

MAGEE, DI ;

VALENTA, Z .

CANADIAN JOURNAL OF CHEMISTRY, 1989, 67 (12) :2237-2240

[10] Bis(trifluoromethane)sulfonimide initiated ring-opening polymerization of octamethylcyclotetrasiloxane [J].

Desmurs, JR ;

Ghosez, L ;

Martins, J ;

Deforth, T ;

Mignani, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 646 (1-2) :171-178

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