Zn-alkynylide additions to acyl iminiums

被引：93

作者：

Fischer, C ^{[1
]}

Carreira, EM ^{[1
]}

机构：

[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 09期

关键词：

D O I：

10.1021/ol049578u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new addition reaction of zinc-alkynyl ides to N-acyl and N-phosphinoyl iminiums is reported. These can be prepared in situ from imines with acid halides in the presence of a Zn-acetylide. The reaction is general with regard to imine, alkyne, and acid halides, allowing access to a large number of differentially protected propargylic amines.

引用

页码：1497 / 1499

页数：3

共 67 条

[11] Regioselective synthesis of gamma-functional propargylic primary amines via organometallic compounds - Uses of the synthesized amines
Courtois, G
Desre, V
Miginiac, L
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 570 (02) : 279 - 292
[12] Efficient asymmetric synthesis of 1-alk-2-yne-1,4-diols
Diez, RS
Adger, B
Carreira, EM
[J]. TETRAHEDRON, 2002, 58 (41) : 8341 - 8344
[13] Asymmetric synthesis of γ-hydroxy α,β-unsaturated aldehydes via enantioselective direct addition of propargyl acetate to aldehydes
El-Sayed, E
Anand, NK
Carreira, EM
[J]. ORGANIC LETTERS, 2001, 3 (19) : 3017 - 3020
[14] STEREOCHEMICAL AND CONFORMATIONAL EFFECTS ON THE CYCLOAROMATIZATION OF DYNEMICIN-A RELATED MOLECULES
ELBAUM, D
PORCO, JA
STOUT, TJ
CLARDY, J
SCHREIBER, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) : 211 - 225
[15] 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
[16] Chelation-controlled stannylacetylene additions to β-alkoxy aldehydes promoted by alkylaluminum halide Lewis acids
Evans, DA
Halstead, DP
Allison, BD
[J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4461 - 4462
[17] Fässler R, 2002, ANGEW CHEM INT EDIT, V41, P3054, DOI 10.1002/1521-3773(20020816)41:16<3054::AID-ANIE3054>3.0.CO
[18] 2-B
[19] Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
Ferraris, D
Young, B
Dudding, T
Lectka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) : 4548 - 4549
[20] 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

← 1 2 3 4 5 6 7 →