An enantioselective synthesis of β2-amino acid derivatives

被引：33

作者：

Elaridi, J ^{[1
]}

Thaqi, A ^{[1
]}

Prosser, A ^{[1
]}

Jackson, WR ^{[1
]}

Robinson, AJ ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Ctr Green Chem, Clayton, Vic 3800, Australia

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 07期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1016/j.tetasy.2005.01.048

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Enantioselective hydrogenation of a series of (E)-alpha-substituted beta-amidoacrylates using Rh(I)-catalysts with chiral phosphine ligands (BPE, DuPHOS) gives beta(2)-amino acid derivatives with enantioselectivities of up to 67%. A beta(2,3)-amino acid derivative was also synthesised with similar enantioselectivity (<= 65%) from the corresponding prochiral enamide. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1309 / 1319

页数：11

共 82 条

[41]

LAUE T, 2000, NAMED ORGANIC REACTI

[42] Efficient synthesis of enantionmerically pure β2-amino acids via chiral isoxazolidinones [J].

Lee, HS ;

Park, JS ;

Kim, BM ;

Gellman, SH .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1575-1578

[43] Rh(I)-catalyzed enantioselective hydrogenation of (E)- and (Z)-β-(acylamino)acrylates using 1,4-bisphosphine ligands under mild conditions [J].

Lee, S ;

Zhang, YJ .

ORGANIC LETTERS, 2002, 4 (14) :2429-2431

[44] Convenient and stereospecific homologation of N-fluorenyl-methoxycarbonyl-alpha-amino acids to their beta-homologues [J].

Leggio, A ;

Liguori, A ;

Procopio, A ;

Sindona, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (13) :1969-1971

[45] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS BASED ON BINAP - RUTHENIUM(II) CATALYZED HYDROGENATION [J].

LUBELL, WD ;

KITAMURA, M ;

NOYORI, R .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :543-554

[46] Solid phase synthesis of beta-peptides via Arndt-Eistert homologation of Fmoc-protected amino acid diazoketones [J].

Marti, RE ;

Bleicher, KH ;

Bair, KW .

TETRAHEDRON LETTERS, 1997, 38 (35) :6145-6148

[47] MIGRATION OF ELECTRONEGATIVE SUBSTITUENTS .1. RELATIVE MIGRATORY APTITUDE AND MIGRATION TENDENCY OF CARBETHOXY GROUP IN DIENONE-PHENOL REARRANGEMENT [J].

MARX, JN ;

ARGYLE, JC ;

NORMAN, LR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2121-2129

[48]

Matthews JL, 1997, LIEBIGS ANN-RECL, P1371

[49] β2/β3-di- and α/β3-tetrapeptide derivatives as potent agonists at somatostatin sst4 receptors [J].

Nunn, C ;

Rueping, M ;

Langenegger, D ;

Schuepbach, E ;

Kimmerlin, T ;

Micuch, P ;

Hurth, K ;

Seebach, D ;

Hoyer, D .

NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 2003, 367 (02) :95-103

[50] Highly enantioselective rhodium-catalyzed hydrogenation of β-dehydroamino acid derivatives using monodentate phosphoramidites [J].

Peña, D ;

Minnaard, AJ ;

de Vries, JG ;

Feringa, BL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (49) :14552-14553

← 1 2 3 4 5 6 7 8 9 →