Diastereoselective synthesis of 1-aryl-2-amino-cyclopropane carboxylates

被引：17

作者：

Melby, Trude ^{[1
]}

Hughes, Rachael Anne ^{[1
]}

Hansen, Tore ^{[1
]}

机构：

[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

来源：

SYNLETT | 2007年 / 14期

关键词：

cyclopropanation; diastereoselective; rhodium; diazoacetates; amino-cyclopropanes;

D O I：

10.1055/s-2007-985587

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methyl 1-aryl-2-amino-cyclopropane carboxylates have been readily synthesized in high yields by Rh-catalyzed decomposition of aryldiazoacetates in the presence of N-vinylphthalimide. The reaction is highly trans-selective.

引用

页码：2277 / 2279

页数：3

共 15 条

[1] Catalytic cyclopropanation of alkenes using diazo compounds generated in situ. A novel route to 2-arylcyclopropylamines [J].

Aggarwal, VK ;

de Vicente, J ;

Bonnert, RV .

ORGANIC LETTERS, 2001, 3 (17) :2785-2788

[2] Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen [J].

Davies, HML ;

Nagashima, T ;

Klino, JL .

ORGANIC LETTERS, 2000, 2 (06) :823-826

[3] Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates [J].

Davies, HML ;

Townsend, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) :6595-6603

[4] Effect of carbenoid structure on the reactivity of rhodium-stabilized carbenoids [J].

Davies, HML ;

Hedges, LM ;

Matasi, JJ ;

Hansen, T ;

Stafford, DG .

TETRAHEDRON LETTERS, 1998, 39 (25) :4417-4420

[5] Effect of diazoalkane structure on the stereoselectivity of rhodium(II) (S)-N-(arylsulfonyl)prolinate catalyzed cyclopropanations [J].

Davies, HML ;

Bruzinski, PR ;

Fall, MJ .

TETRAHEDRON LETTERS, 1996, 37 (24) :4133-4136

[6] Enantioselective synthesis of novel homochiral alpha-substituted (S)-isoserine derivatives. Incorporation of this amino acid in a highly conformationally constrained dipeptide surrogate [J].

Diaz, M ;

Ortuno, RM .

TETRAHEDRON-ASYMMETRY, 1996, 7 (12) :3465-3478

[7] Enantioselective synthesis of novel, highly conformationally constrained peptide surrogates [J].

Diaz, M ;

Jimenez, JM ;

Ortuno, RM .

TETRAHEDRON-ASYMMETRY, 1997, 8 (14) :2465-2471

[8]

Doyle M. P., 1998, MODERN CATALYTIC MET, P163

[9] Foldamers: A manifesto [J].

Gellman, SH .

ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180

[10] Synthesis and applications of β-aminocarboxylic acids containing a cyclopropane ring [J].

Gnad, F ;

Reiser, O .

CHEMICAL REVIEWS, 2003, 103 (04) :1603-1623

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