Catalytic, enantioselective, conjugate alkyne addition

被引：164

作者：

Knöpfel, TF ^{[1
]}

Zarotti, P ^{[1
]}

Ichikawa, T ^{[1
]}

Carreira, EM ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 27期

关键词：

D O I：

10.1021/ja052411r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We document a copper-catalyzed, enantioselective, conjugate addition involving the direct use of a terminal acetylene, which undergoes in situ metalation. The addition reactions of phenylacetylene to Meldrum's acid derived acceptors take place in aqueous media, without recourse to inert atmosphere. The success of the enantioselective process was enabled by the use of a new class of conveniently accessed P,N-ligands, which we have termed PINAP. These modular ligands are responsive to numerous electronic and steric modifications that permit optimization of the reaction. Copyright © 2005 American Chemical Society.

引用

页码：9682 / 9683

页数：2

共 50 条

[1] Catalytic enantioselective conjugate addition of carbamates
Palomo, C
Oiarbide, M
Halder, R
Kelso, M
Gómez-Bengoa, E
García, JM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) : 9188 - 9189
[2] Catalytic enantioselective conjugate addition of carbamates
1600, American Chemical Society, Columbus, United States (126):
[3] Catalytic enantioselective conjugate addition with Grignard reagents
Lopez, Fernando
Minnaard, Adriaan J.
Feringa, Ben L.
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (03) : 179 - 188
[4] A catalytic enantioselective conjugate addition of cyanide to enones
Tanaka, Yuta
Kanai, Motomu
Shibasaki, Masakatsu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (19) : 6072 - +
[5] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINC COMPOUNDS TO CHALCONES
BOLM, C
EWALD, M
FELDER, M
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1205 - 1215
[6] Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents
Feringa, BL
Pineschi, M
Arnold, LA
Imbos, R
de Vries, AHM
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) : 2620 - 2623
[7] Catalytic enantioselective conjugate addition of indoles to simple α,β-unsaturated ketones
Bandini, M
Fagioli, M
Melchiorre, P
Melloni, A
Umani-Ronchi, A
TETRAHEDRON LETTERS, 2003, 44 (31) : 5843 - 5846
[8] Highly enantioselective, catalytic conjugate addition of cyanide to α,β-unsaturated Imides
Sammis, GM
Jacobsen, EN
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (15) : 4442 - 4443
[9] Catalytic enantioselective conjugate addition en route to paxilline indoloterpenoids
Schatz, Devon J.
Li, Wenqin
Pronin, Sergey, V
TETRAHEDRON, 2019, 75 (24) : 3361 - 3365
[10] CATALYTIC ASYMMETRIC INDUCTION IN ENANTIOSELECTIVE CONJUGATE ADDITION OF DIALKYLZINCS TO ENONES
SOAI, K
YOKOYAMA, S
HAYASAKA, T
EBIHARA, K
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17): : 4148 - 4149

← 1 2 3 4 5 →