Asymmetric synthesis of 3-substituted pyrrolidones via α-alkylation of a chiral non-racemic γ-lactam

被引：29

作者：

Baussanne, I ^{[1
]}

Travers, C ^{[1
]}

Royer, J ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(98)00024-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

3-Alkyl pyrrolidones 9 were synthesized in good yield and high diastereoselectivity by oc-alkylation of the new chiral non-racemic lactam 8 derived from (R)-(-)-phenylglycinol. After debenzylation and introduction of an electron-withdrawing group, 3-methylpyrrolidone 10 is easily hydrolyzed in a basic medium to produce gamma-aminobutyric acid (GABA) analogue 13. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：797 / 804

页数：8

共 65 条

[1] AN IMPROVED, CONVENIENT PROCEDURE FOR REDUCTION OF AMINO-ACIDS TO AMINOALCOHOLS - USE OF NABH4-H2SO4 [J].

ABIKO, A ;

MASAMUNE, S .

TETRAHEDRON LETTERS, 1992, 33 (38) :5517-5518

[2] SYNTHESIS OF CHIRAL 1,2,4-TRIAMINOBUTANES [J].

ALTMAN, J ;

BENISHAI, D .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :91-100

[3] ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .14. PREPARATION OF ENANTIOMERICALLY PURE (3S,4S)-STATINE AND (3S,4R)-STATINE DERIVATIVES [J].

ANDREW, RG ;

CONROW, RE ;

ELLIOTT, JD ;

JOHNSON, WS ;

RAMEZANI, S .

TETRAHEDRON LETTERS, 1987, 28 (52) :6535-6538

[4] ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING [J].

ARSENIYADIS, S ;

HUANG, PQ ;

PIVETEAU, D ;

HUSSON, HP .

TETRAHEDRON, 1988, 44 (09) :2457-2470

[5] AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL [J].

BALDWIN, JE ;

MIRANDA, T ;

MOLONEY, M ;

HOKELEK, T .

TETRAHEDRON, 1989, 45 (23) :7459-7468

[6] CRYSTAL AND MOLECULAR-STRUCTURE OF A THF-SOLVATED LITHIUM AMIDE ENOLATE DIMER [J].

BAUER, W ;

LAUBE, T ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (02) :764-773

[7] Asymmetric routes towards polyfunctionalized pyrrolidines: Synthesis and reactivity of a chiral silyloxypyrrole. [J].

Baussanne, I ;

Royer, J .

TETRAHEDRON LETTERS, 1996, 37 (08) :1213-1216

[8] DIASTEREOSELECTIVE BIS-ALKYLATION OF CHIRAL NON-RACEMIC ALPHA,BETA-UNSATURATED GAMMA-LACTAMS [J].

BAUSSANNE, I ;

CHIARONI, A ;

HUSSON, HP ;

RICHE, C ;

ROYER, J .

TETRAHEDRON LETTERS, 1994, 35 (23) :3931-3934

[9] Synthesis of aza-muricatacin: An analogue of the bioactive muricatacin an acetogenin of annonaceae [J].

Baussanne, I ;

Schwardt, O ;

Royer, J ;

Pichon, M ;

Figadere, B ;

Cave, A .

TETRAHEDRON LETTERS, 1997, 38 (13) :2259-2262

[10] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF 3-ETHYL AND 3-NORMAL-PROPYLPYRROLIDINE [J].

BETTONI, G ;

CELLUCCI, C ;

BERARDI, F .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (03) :603-605

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