Asymmetric synthesis of α-amino acids from α,β-(Z)-didehydroamino acid derivatives with 1,2,3,6-tetrahydropyrazin-2-one structure

被引：35

作者：

Abellán, T ^{[1
]}

Mancheño, B ^{[1
]}

Nájera, C ^{[1
]}

Sansano, JM ^{[1
]}

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 30期

关键词：

amino acids; pyrazinones; asymmetric synthesis; phase-transfer catalysis; DDAA derivatives; Knoevenagel condensation; cyclopropanation; Heck reaction; enaminones; Diels-Alder reaction;

D O I：

10.1016/S0040-4020(01)00553-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral (Z)-alpha,beta -didehydroamino acid (DDAA) derivatives 14, 15 and 16 are obtained from a new chiral iminic cyclic glycine template with 1,2,3,6-tetrahydropyrazin-2-one structure 10 by condensation with carbonyl compounds, Eschenmoser's salt and Bredereck's reagent, respectively. The didehydroalanine derivative 15 and the enaminone 16 can give DDAA derivatives 14 using Heck olefination and vinylic nucleophilic substitution. These DDAA derivatives 14 and 15 undergo diastereoselective cyclopropanation, 1,3-dipolar and Diels-Alder cycloaddition reactions giving, after hydrolysis, the corresponding cyclic and bicyclic oc-amino acids. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6627 / 6640

页数：14

共 75 条

[21] ASYMMETRIC-SYNTHESIS OF 2-AMINONORBORNANE-2-CARBOXYLIC ACIDS BY DIELS-ALDER REACTION
CATIVIELA, C
LOPEZ, P
MAYORAL, JA
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1295 - 1304
[22] Stereoselective synthesis of quaternary α-amino acids.: Part 2.: Cyclic compounds
Cativiela, C
Díaz-de-Villegas, MD
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (03) : 645 - 732
[23] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds
Cativiela, C
Diaz-de-Villegas, MD
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (20) : 3517 - 3599
[24] A SIMPLE SYNTHESIS OF (-)-(1S,2R)-ALLOCORONAMIC ACID IN ITS ENANTIOMERICALLY PURE FORM
CATIVIELA, C
DIAZDEVILLEGAS, MD
JIMENEZ, AI
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (01) : 177 - 182
[25] Chai CLL, 1997, J CHEM RES-S, P382
[26] METHYLENE PIPERAZINE-2,5-DIONES AS TEMPLATES FOR THE SYNTHESIS OF AMINO-ACID DERIVATIVES
CHAI, CLL
KING, AR
[J]. TETRAHEDRON LETTERS, 1995, 36 (24) : 4295 - 4298
[27] Stereocontrolled intermolecular radical additions to methylidenepiperazine-2,5-diones
Chai, CLL
King, AR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (09): : 1173 - 1182
[28] Asymmetric synthesis of substituted 1-aminocyclopropane-1-carboxylic acids from a new chiral glycine equivalent with 3,6-dihydro-2H-1,4-oxazin-2-one structure
Chinchilla, R
Falvello, LR
Galindo, N
Nájera, C
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2223 - 2227
[29] Asymmetric synthesis of (S)-α-methyl α-amino acids by alkylation of chiral 3,6-dihydro-2H-1,4-oxazin-2-ones using unactivated alkyl halides and organic bases
Chinchilla, R
Galindo, N
Nájera, C
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (16) : 2769 - 2772
[30] Asymmetric synthesis of alpha-methyl alpha-amino acids by diastereoselective alkylation of optically active 6-isopropyl-3-methyl-2,3-dihydro-6H-1,4-oxazin-2-ones
Chinchilla, R
Falvello, LR
Galindo, N
Najera, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (09): : 995 - 997

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