γ-selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis

被引：96

作者：

Tominaga, S ^{[1
]}

Oi, Y ^{[1
]}

Kato, T ^{[1
]}

An, DK ^{[1
]}

Okamoto, S ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Appl Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 29期

关键词：

allylic substitution; organocopper; N-heterocyclic carbene; asymmetric reaction;

D O I：

10.1016/j.tetlet.2004.05.135

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of allylic compounds with alkyl Grignard reagents in the presence of a catalytic amount of copper N-heterocyclic carbene (NHC) complexes proceeded predominantly in an S(N)2' reaction pathway to give gamma-substituted product in excellent yield. The method was applied to asymmetric reaction by using optically active NHC ligands. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5585 / 5588

页数：4

共 24 条

[1] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition [J].

Alexakis, A ;

Winn, CL ;

Guillen, F ;

Pytkowicz, J ;

Roland, S ;

Mangeney, P .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) :345-348

[2] Tandem copper-catalyzed enantioselective allylation-metathesis [J].

Alexakis, A ;

Croset, K .

ORGANIC LETTERS, 2002, 4 (23) :4147-4149

[3]

Alexakis A, 2001, SYNLETT, P927

[4]

CROSET K, 2004, ANGEW CHEM INT EDIT, V43, P2426

[5] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[6] Highly enantioselective copper-catalyzed substitution of allylic chlorides with diorganozincs [J].

Dübner, F ;

Knochel, P .

TETRAHEDRON LETTERS, 2000, 41 (48) :9233-9237

[7]

Dübner F, 1999, ANGEW CHEM INT EDIT, V38, P379, DOI 10.1002/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO

[8]

2-Y

[9] Strong ligand accelerated catalysis by an Arduengo-type carbene in copper-catalysed conjugate addition [J].

Fraser, PK ;

Woodward, S .

TETRAHEDRON LETTERS, 2001, 42 (14) :2747-2749

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

Guillen, F ;

Winn, CL ;

Alexakis, A .

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

← 1 2 3 →