Truncated diastereoselective Passerini reaction, a rapid construction of polysubstituted oxazole and peptides having α-hydroxy-β-amino acid component

被引：43

作者：

Cuny, G ^{[1
]}

Gámez-Montaño, R ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 22期

关键词：

diastereoselectivity; N; N-dibenzyl aminoaldehyde; (alpha-hydroxy-beta-amino acid; multicomponent reaction; oxazole; Passerini reaction;

D O I：

10.1016/j.tet.2004.03.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of aldehydes and ketones, including aliphatic and aromatic ones, with amides of alpha-isocyano-beta-phenylpropionic acid in toluene in the presence of lithium bromide gives 2,4,5-trisubstituted oxazoles in good to excellent yield. Protected chiral alpha-amino aldehydes participate in this reaction to give, after hydrolysis of the oxazoles, norstatine-containing peptides in good overall yield. The nucleophilic addition of isonitriles to N,N-dibenzyl phenylalanal is investigated for the first time and is found to be stereoselective leading predominantly to the anti-adduct (dr=9/1). On the other hand, the reaction between the N-Boc phenylalanal and isonitrile is non-stereoselective. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4879 / 4885

页数：7

共 53 条

[1] Stereocontrolled asymmetric synthesis of α-hydroxy-β-amino acids.: A stereodivergent approach [J].

Aoyagi, Y ;

Jain, RP ;

Williams, RM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (15) :3472-3477

[2] Pd-assisted multicomponent synthesis of heterocycles [J].

Balme, G ;

Bossharth, E ;

Monteiro, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111

[3] Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes [J].

Banfi, L ;

Guanti, G ;

Riva, R ;

Basso, A ;

Calcagno, E .

TETRAHEDRON LETTERS, 2002, 43 (22) :4067-4069

[4] Passerini multicomponent reaction of protected α-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors [J].

Banfi, L ;

Guanti, G ;

Riva, R .

CHEMICAL COMMUNICATIONS, 2000, (11) :985-986

[5] Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction [J].

Basso, A ;

Banfi, L ;

Riva, R ;

Piaggio, P ;

Guanti, G .

TETRAHEDRON LETTERS, 2003, 44 (11) :2367-2370

[6] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[7]

CHEREST M, 1968, TETRAHEDRON LETT, P2205

[8]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[9] HETEROCYCLIZATION OF ALPHA ACYLAMINOAMIDES .4. MECHANISMS FOR OPENING AND FORMATION OF 5-AMINOOXAZOLE CYCLE [J].

CLERIN, D ;

KILLE, G ;

FLEURY, JP .

TETRAHEDRON, 1974, 30 (03) :469-474

[10] A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular SNAr-based cycloetherification [J].

Cristau, P ;

Vors, JP ;

Zhu, JP .

ORGANIC LETTERS, 2001, 3 (25) :4079-4082

← 1 2 3 4 5 6 →