Tandem copper-catalyzed enantioselective allylation-metathesis

被引：99

作者：

Alexakis, A ^{[1
]}

Croset, K ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 23期

关键词：

D O I：

10.1021/ol0269244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Grignard reagents undergo enantioselective (up to 86% ee) copper-catalyzed S(N)2' substitution on achiral allylic chlorides. The reaction is wide in scope for both the Grignard reagent and the allylic substrate. The resulting terminal alkene could be submitted to intra- or intermolecular metathesis to afford new chiral synthons. The experimental conditions are compatible with a one-pot overall substitution-metathesis procedure without loss of enantioselectivity.

引用

页码：4147 / 4149

页数：3

共 17 条

[1] Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions
Alexakis, A
Benhaim, C
Rosse, S
Humam, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) : 5262 - 5263
[2] Alexakis A, 2001, SYNLETT, P927
[3] Alexakis A, 2001, SYNLETT, P1375
[4] Breit B, 2002, MODERN ORGANOCOPPER CHEMISTRY, P188, DOI 10.1002/3527600086.ch6
[5] Highly enantioselective copper-catalyzed substitution of allylic chlorides with diorganozincs
Dübner, F
Knochel, P
[J]. TETRAHEDRON LETTERS, 2000, 41 (48) : 9233 - 9237
[6] Dübner F, 1999, ANGEW CHEM INT EDIT, V38, P379, DOI 10.1002/(SICI)1521-3773(19990201)38:3<379::AID-ANIE379>3.0.CO
[7] 2-Y
[8] Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition
Feringa, BL
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 346 - 353
[9] Karlström ASE, 2002, MODERN ORGANOCOPPER CHEMISTRY, P259, DOI 10.1002/3527600086.ch8
[10] Karlström ASE, 2001, SYNLETT, P923

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