Highly efficient phosphine-catalyzed aza-Michael reactions of α,β-unsaturated compounds with carbamates in the presence of TMSCl

被引：64

作者：

Xu, LW ^{[1
]}

Xia, CG ^{[1
]}

机构：

[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 23期

关键词：

conjugate addition; aza-Michael; carbamates; enones; phosphine;

D O I：

10.1016/j.tetlet.2004.04.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aza-Michael reactions of enones with carbamates took place efficiently in the presence of a catalytic amount of phosphine and TMSCI to afford the total products in high yields. The new catalytic system was also efficient in the aza-Michael reaction of chalcone, which was difficult to react with carbamates by transition metal salts catalysts. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4507 / 4510

页数：4

共 58 条

[1]

Abele S, 2000, EUR J ORG CHEM, V2000, P1

[2] Sulfonation with inversion by Mitsunobu reaction: An improvement on the original conditions [J].

Anderson, NG ;

Lust, DA ;

Colapret, KA ;

Simpson, JH ;

Malley, MF ;

Gougoutas, JZ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22) :7955-7958

[3]

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

[4]

2-E

[5] Highly diastereoselective conjugate addition of lithium dialkylamides to alpha,beta-unsaturated esters having a chiral center at the gamma-position [J].

Asao, N ;

Shimada, T ;

Sudo, T ;

Tsukada, N ;

Yazawa, K ;

Gyoung, YS ;

Uyehara, T ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6274-6282

[6] 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

[7]

Bull SD, 2000, SYNLETT, P1257

[8]

Christmann M, 2000, ANGEW CHEM INT EDIT, V39, P4364, DOI 10.1002/1521-3773(20001201)39:23<4364::AID-ANIE4364>3.0.CO

[9]

2-G

[10] A novel synthesis of α-amino acid derivatives through catalytic, enantioselective ene reactions of α-imino esters [J].

Drury, WJ ;

Ferraris, D ;

Cox, C ;

Young, B ;

Lectka, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :11006-11007

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