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

[1] Synthesis of new chiral N-heterocyclic carbene-imine ligands and their application to an asymmetric allylic alkylation reaction [J].

Bonnet, LG ;

Douthwaite, RE ;

Kariuki, BM .

ORGANOMETALLICS, 2003, 22 (21) :4187-4189

[2] New N-heterocyclic carbene ligand and its application in asymmetric nickel-catalyzed aldehyde/alkyne reductive couplings [J].

Chaulagain, Mani Raj ;

Sormunen, Grant J. ;

Montgomery, John .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (31) :9568-+

[3] Surprising role of aryl halides in nickel-catalyzed reductive aldol reactions [J].

Chrovian, Christa C. ;

Montgomery, John .

ORGANIC LETTERS, 2007, 9 (03) :537-540

[4] Highly enantioselective one-pot, three-component imino-reformatsky reaction [J].

Cozzi, PG ;

Rivalta, E .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3600-3603

[5] Synthesis and stereochemistry of the first chiral (imidazolinylidene)- and (triazolinylidene)palladium(II) complexes [J].

Enders, D ;

Gielen, H ;

Raabe, G ;

Runsink, J ;

Teles, JH .

CHEMISCHE BERICHTE-RECUEIL, 1996, 129 (12) :1483-1488

[6] Highly active chiral ruthenium catalysts for asymmetric ring-closing olefin metathesis [J].

Funk, TW ;

Berlin, JM ;

Grubbs, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1840-1846

[7]

Gade LH, 2007, TOP ORGANOMETAL CHEM, V21, P117, DOI 10.1007/3418_028

[8] Enantioselective copper-catalyzed conjugate addition using chiral diaminocarbene ligands [J].

Guillen, F ;

Winn, CL ;

Alexakis, A .

TETRAHEDRON-ASYMMETRY, 2001, 12 (15) :2083-2086

[9]

Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

[10]

2-Y

← 1 2 3 4 →