Highly enantioselective copper-phosphoramidite-catalyzed conjugate addition of dialkylzinc reagents to acyclic α,β-unsaturated imides

被引：25

作者：

Pineschi, M ^{[1
]}

Del Moro, F ^{[1
]}

Di Bussolo, V ^{[1
]}

Macchia, F ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 03期

关键词：

asymmetric catalysis; C-C bond formation; conjugate addition; copper; phosphoramidite ligands; zinc;

D O I：

10.1002/adsc.200505309

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new and practical way to introduce an alkyl fragment in the beta-position of aliphatic carboxylic acid derivatives with high enantioselectivities by the use of a commercially available chiral ligand is reported. N-Acylpyrrolidinones, as simple derivatives of an alpha,beta-unsaturated carboxylic acid, were found to be the substrates of choice featuring good reactivity and high en antioselectivities (up to > 99% ee).

引用

页码：301 / 304

页数：4

共 50 条

[31] Copper hydride catalyzed enantioselective conjugate reduction of unsaturated nitriles
Lee, Daehyung
Yang, Youngmin
Yun, Jaesook
SYNTHESIS-STUTTGART, 2007, (14): : 2233 - 2235
[32] Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides
Escorihuela, Jorge
Burguete, M. Isabel
Luis, Santiago V.
TETRAHEDRON LETTERS, 2008, 49 (48) : 6885 - 6888
[33] Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: Construction of chiral quaternary centers
Vuagnoux-d'Augustin, Magali
Alexakis, Alexandre
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (34) : 9647 - 9662
[34] Enantioselective copper-catalyzed conjugate addition to trisubstituted cyclohexenones: Construction of stereogenic quaternary centers
d'Augustin, M
Palais, L
Alexakis, A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (09) : 1376 - 1378
[35] Multinuclear Catalyst for Copper-Catalyzed Asymmetric Conjugate Addition of Organozinc Reagents
Endo, Kohei
Ogawa, Mika
Shibata, Takanori
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) : 2410 - 2413
[36] Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite-Catalyzed Allylic Alkylation with Organolithium Reagents
Fananas-Mastral, Martin
Perez, Manuel
Bos, Pieter H.
Rudolph, Alena
Harutyunyan, Syuzanna R.
Feringa, Ben L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (08) : 1922 - 1925
[37] Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminum to β,γ-Unsaturated α-Ketoamides: Efficient Access to γ-Methyl-Substituted Carbonyl Compounds
Goncalves-Contal, Sylvie
Gremaud, Ludovic
Alexakis, Alexandre
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) : 12701 - 12704
[38] Copper(I)-Catalyzed Enantioselective 1,4-Conjugate Hydrophosphination of α,β-Unsaturated Esters
Wang, Ye
Wang, Zi-Qing
Yin, Liang
SYNTHESIS-STUTTGART, 2023, 55 (14): : 2228 - 2240
[39] Enantioselective synthesis: of chiral γ-aryl α-keto ester by copper-catalyzed 1,4-conjugate addition using D2-symmetric biphenyl phosphoramidite ligand
Yang, Bo
Xie, Fang
Yu, Han
Shen, Kaiji
Ma, Zhenni
Zhang, Wanbin
TETRAHEDRON, 2011, 67 (34) : 6197 - 6201
[40] Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones
Ma, Zhenni
Xie, Fang
Yu, Han
Zhang, Yiren
Wu, Xiaoting
Zhang, Wanbin
CHEMICAL COMMUNICATIONS, 2013, 49 (46) : 5292 - 5294

← 1 2 3 4 5 →