Asymmetric synthesis of 3-substituted proline chimeras bearing polar side chains of proteinogenic amino acids

被引：43

作者：

Quancard, J ^{[1
]}

Labonne, A ^{[1
]}

Jacquot, Y ^{[1
]}

Chassaing, G ^{[1
]}

Lavielle, S ^{[1
]}

Karoyan, P ^{[1
]}

机构：

[1] Univ Paris 06, CNRS, UMR 7613, F-75252 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 23期

关键词：

D O I：

10.1021/jo048762q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The amino-zinc-ene-enolate cyclization reaction is a straightforward route to the synthesis of 3-substituted prolines. Herein we report the application of this reaction to the syntheses of proline chimeras of lysine, glutamic acid, glutamine, arginine, and serine. All these compounds were obtained in enantiomerically pure form and suitably protected for peptide synthesis.

引用

页码：7940 / 7948

页数：9

共 50 条

[21] Efficient asymmetric synthesis of 3-substituted β-sultams [J].

Enders, D ;

Wallert, S .

TETRAHEDRON LETTERS, 2002, 43 (29) :5109-5111

[22] Synthesis of non-proteinogenic (D)- or (L)-amino acids by asymmetric hydrogenation [J].

Kreuzfeld, HJ ;

Dobler, C ;

Schmidt, U ;

Krause, HW .

AMINO ACIDS, 1996, 11 (3-4) :269-282

[23] SYNTHESIS OF AMINO-ACIDS WITH MODIFIED PRINCIPAL PROPERTIES .2. AMINO-ACIDS WITH POLAR SIDE-CHAINS [J].

LARSSON, U ;

CARLSON, R .

ACTA CHEMICA SCANDINAVICA, 1994, 48 (06) :511-516

[24] A Modular Synthesis of Teraryl-Based α-Helix Mimetics, Part 3: Iodophenyltriflate Core Fragments Featuring Side Chains of Proteinogenic Amino Acids [J].

Trobe, Melanie ;

Vareka, Martin ;

Schreiner, Till ;

Dobrounig, Patrick ;

Doler, Carina ;

Holzinger, Ella B. ;

Steinegger, Andreas ;

Breinbauer, Rolf .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (17)

[25] A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds [J].

Soloshonok, VA ;

Cai, CZ ;

Hruby, VJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (12) :2172-+

[26] A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds [J].

Soloshonok, Vadim A. ;

Cai, Chaozhong ;

Hruby, Victor J. .

Angewandte Chemie (International Edition in English), 2000, 39 (12) :2172-2175

[27] A facile synthesis of 3-substituted pipecolic acids [J].

Makara, GM ;

Marshall, GR .

PEPTIDES: FRONTIERS OF PEPTIDES SCIENCE, 1999, :281-282

[28] Organocatalytic asymmetric 5-hydroxypyrrolidine synthesis:: a highly enantioselective route to 3-substituted proline derivatives [J].

Rios, Ramon ;

Ibrahem, Ismail ;

Vesely, Jan ;

Sunden, Henrik ;

Cordova, Armando .

TETRAHEDRON LETTERS, 2007, 48 (49) :8695-8699

[29] SYNTHESIS AND POLYMERIZATION OF THIOPHENES 3-SUBSTITUTED BY CHIRAL CHAINS [J].

SCHULZ, E ;

BETHMONT, V ;

FAHMI, K ;

FACHE, F ;

LEMAIRE, M .

JOURNAL DE CHIMIE PHYSIQUE ET DE PHYSICO-CHIMIE BIOLOGIQUE, 1995, 92 (04) :783-786

[30] Asymmetric Intramolecular α-Arylation of Polar Amino Acids Bearing β-Leaving Groups [J].

Taspinar, Oemer ;

Leonard, Daniel J. ;

Picois, Nathan ;

Goecke, Cornelia ;

Zabka, Matej ;

Sparkes, Hazel A. ;

Clayden, Jonathan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (29)

← 1 2 3 4 5 →