Cu-catalysed asymmetric 1,4-addition of Me3Al to nitroalkenes.: Synthesis of (+)-ibuprofen

被引：50

作者：

Polet, D ^{[1
]}

Alexakis, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 09期

基金：

新加坡国家研究基金会;

关键词：

copper; aluminium; nitro; conjugate addition; asymmetry; ibuprofen;

D O I：

10.1016/j.tetlet.2005.01.007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trimethylaluminium undergoes enantioselective (ee up to 93%) copper-catalysed Michael addition to various nitroalkenes. Copper thiophenecarboxylate (CuTC) (2 mol %) and 4 mol% of a chiral phosphoramidite ligand are sufficient for a complete and clean reaction. The synthesis of (+)-ibuprofen is described with 82% ee. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1529 / 1532

页数：4

共 36 条

[1] Alexakis A, 2004, ACS SYM SER, V880, P43
[2] Biphenol-based phosphoramidite ligands for the enantioselective copper-catalyzed conjugate addition of diethylzinc
Alexakis, A
Polet, D
Rosset, S
March, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) : 5660 - 5667
[3] Biphenol-based ligands for Cu-catalyzed asymmetric conjugate addition
Alexakis, A
Polet, D
Benhaim, C
Rosset, S
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2199 - 2203
[4] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition
Alexakis, A
Winn, CL
Guillen, F
Pytkowicz, J
Roland, S
Mangeney, P
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) : 345 - 348
[5] 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
[6] Alexakis A, 2001, SYNLETT, P1375
[7] Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)(2) or trivalent phosphorus ligands
Alexakis, A
Vastra, J
Mangeney, P
[J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7745 - 7748
[8] Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221
[9] Enantioselective copper-catalyzed conjugate addition of dialkyl zinc to nitro-olefins
Alexakis, A
Benhaim, C
[J]. ORGANIC LETTERS, 2000, 2 (17) : 2579 - 2581
[10] ALEXAKIS A, 2005, ANGEW CHEM INT ED, V44

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