Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and silanes using chiral N-heterocyclic carbenes as ligands

被引：103

作者：

Sato, Yoshihiro ^{[1
]}

Hinata, Yu ^{[1
]}

Seki, Reiko ^{[1
]}

Oonishi, Yoshihiro ^{[1
]}

Saito, Nozomi ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 26期

关键词：

D O I：

10.1021/ol702543m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel(0)-catalyzed asymmetric three-component coupling of 1,3-dienes, aldehydes, and silanes has been realized utilizing a chiral N-heterocyclic. carbene as a ligand. On the basis of the screening of various NHC precursors, an imidazolium salt having 1-(2,4,6-trimethylphenyl)propyl groups on the nitrogen was designed and synthesized. In this reaction, various coupling products were produced in good yields with high regio-, diastereo- (anti selective in the case of the internal 1,3-diene), and enantioselectivities (up to 97% ee).

引用

页码：5597 / 5599

页数：3

共 39 条

[21] Lewis base activation of Grignard reagents with N-heterocyclic carbenes.: Cu-free catalytic enantioselective additions to γ-chloro-α,β-unsaturated esters [J].

Lee, Yunmi ;

Hoveyda, Amir H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15604-15605

[22] Asymmetric addition of aryl boron reagents to enones with rhodium dicyclophane imidazolium carbene catalysis [J].

Ma, YD ;

Song, C ;

Ma, CQ ;

Sun, ZJ ;

Chai, Q ;

Andrus, MB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (47) :5871-5874

[23] Ligand-dependent scope and divergent mechanistic behavior in nickel-catalyzed reductive couplings of aldehydes and alkynes [J].

Mahandru, GM ;

Liu, G ;

Montgomery, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3698-3699

[24] Copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted enones. Construction of all-carbon quaternary chiral centers [J].

Martin, David ;

Kehrli, Stefan ;

d'Augustin, Magali ;

Clavier, Herve ;

Mauduit, Marc ;

Alexakis, Alexandre .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8416-8417

[25] Catalytic asymmetric reductive coupling of alkynes and aldehydes:: Enantioselective synthesis of allylic alcohols and α-hydroxy ketones [J].

Miller, KM ;

Huang, WS ;

Jamison, TF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (12) :3442-3443

[26] Nickel-catalyzed reductive cyclizations and couplings [J].

Montgomery, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3890-3908

[27] Nickel-catalyzed cyclizations, couplings, and cycloadditions involving three reactive components [J].

Montgomery, J .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (07) :467-473

[28] Nickel-catalyzed coupling of alkenes, aldehydes, and silyl triflates [J].

Ng, Sze-Sze ;

Ho, Chun-Yu ;

Jamison, Timothy F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (35) :11513-11528

[29]

Nolan S. P., 2006, N HETEROCYCLIC CARBE, DOI DOI 10.2174/1570180813666160826100158

[30] Chiral N-heterocyclic carbene-transition metal complexes in asymmetric catalysis [J].

Perry, MC ;

Burgess, K .

TETRAHEDRON-ASYMMETRY, 2003, 14 (08) :951-961

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