Synthesis of enantiomerically enriched propargylamines by copper-catalyzed addition of alkynes to enamines

被引：124

作者：

Koradin, C ^{[1
]}

Gommermann, N ^{[1
]}

Polborn, K ^{[1
]}

Knochel, P ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 12期

关键词：

alkynes; amines; asymmetric catalysis; C-H activation; copper catalysis;

D O I：

10.1002/chem.200204691

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first copper(I) bromide/ Quinap-catalyzed synthesis of enantiomerically enriched propargylamines by addition of alkynes to enamines is reported. Various functionalized terminal alkynes add smoothly to N-protected enamines to afford the corresponding amines in good to high yields and moderate to good enantiomeric excesses. The influence of the metal salt, the ligand, and the protecting group on the conversion, the reaction rate, and the stereoselectivity of the reaction are investigated. The scope of the reaction and further transformations of the resulting propargylamines (deprotection, Pauson-Khand reaction) are also described.

引用

页码：2797 / 2811

页数：15

共 43 条

[11] ENANTIOSELECTIVE SYNTHESIS OF ALLYL-AMINES, PROPARGYL-AMINES, AND 4-EN-2-YNYL-AMINES VIA 1,2-ADDITION OF ORGANOCERIUM REAGENTS TO CHIRAL ALDEHYDE IMINES
ENDERS, D
SCHANKAT, J
[J]. HELVETICA CHIMICA ACTA, 1995, 78 (04) : 970 - 992
[12] Fernandez E, 2000, CHEM-EUR J, V6, P1840, DOI 10.1002/(SICI)1521-3765(20000515)6:10<1840::AID-CHEM1840>3.0.CO
[13] 2-6
[14] Direct addition of TMS-acetylene to aldimines catalyzed by a simple, commercially available Ir(I) complex
Fischer, C
Carreira, EM
[J]. ORGANIC LETTERS, 2001, 3 (26) : 4319 - 4321
[15] Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes
Frantz, DE
Fässler, R
Carreira, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1806 - 1807
[16] The discovery of novel reactivity in the development of C-C bond-forming reactions:: In situ generation of zinc acetylides with ZnII/R3N
Frantz, DE
Fässler, R
Tomooka, CS
Carreira, EM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 373 - 381
[17] MILD AND SELECTIVE PALLADIUM(0)-CATALYZED DEALLYLATION OF ALLYLIC AMINES - ALLYLAMINE AND DIALLYLAMINE AS VERY CONVENIENT AMMONIA EQUIVALENTS FOR THE SYNTHESIS OF PRIMARY AMINES
GARROHELION, F
MERZOUK, A
GUIBE, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) : 6109 - 6113
[18] Gawley R.E., 1996, PRINCIPLES ASYMMETRI
[19] HABERMEHL G, 1992, NATURSTOFFCHEMIE EIN
[20] HAUSKE JR, 1992, TETRAHEDRON LETT, V33, P3715, DOI 10.1016/0040-4039(92)80006-6

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