Highly enantioselective copper-catalyzed allylic alkylation with phosphoramidite ligands

被引：63

作者：

van Zijl, AW ^{[1
]}

Arnold, LA ^{[1
]}

Minnaard, AJ ^{[1
]}

Feringa, BL ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2004年 / 346卷 / 04期

关键词：

allylic alkylation; asymmetric catalysis; copper; diorganozinc compounds; phosphoramidite ligands; S(N)2 '-substitution;

D O I：

10.1002/adsc.200303207

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

New phosphoramidites were applied as chiral ligands in the Cu-catalyzed allylic alkylation with dialkylzinc reagents. A variety of substrates, reagents and chiral ligands were screened, resulting in improved catalytic methodology for allylic bromides in which enantioselectivities up to 88% were reached.

引用

页码：413 / 420

页数：8

共 62 条

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

Alexakis, A ;

Croset, K .

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

[2]

Alexakis A, 2001, SYNLETT, P927

[3]

Alexakis A, 2001, SYNLETT, P1375

[4]

[Anonymous], ANGEW CHEM

[5] Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; Ligand variation and non-linear effects [J].

Arnold, LA ;

Imbos, R ;

Mandoli, A ;

de Vries, AHM ;

Naasz, R ;

Feringa, BL .

TETRAHEDRON, 2000, 56 (18) :2865-2878

[6]

ARNOLD LA, UNPUB ORG LETT

[7]

Bartels B, 2003, EUR J ORG CHEM, V2003, P1097

[8] Ir-catalysed allylic substitution: mechanistic aspects and asymmetric synthesis with phosphorus amidites as ligands [J].

Bartels, B ;

Helmchen, G .

CHEMICAL COMMUNICATIONS, 1999, (08) :741-742

[9] Highly stereo- and regioselective allylations catalyzed by Mo-pyridylamide complexes: Electronic and steric effects of the ligand [J].

Belda, O ;

Kaiser, NF ;

Bremberg, U ;

Larhed, M ;

Hallberg, A ;

Moberg, C .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5868-5870

[10]

BELLER M, 1909, TRANSITION METALS OR

← 1 2 3 4 5 6 7 →