Synthesis and NMR spectroscopic studies of optically active derivatives of γ-aminobutenoic acids and 2-amino-pyrrolin-4-ones

被引：7

作者：

Petroliagi, M ^{[1
]}

Igglessi-Markopoulou, O ^{[1
]}

机构：

[1] Natl Tech Univ Athens, Dept Chem Engn, Organ Chem Lab, GR-15773 Athens, Greece

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2001年 / 38卷 / 04期

关键词：

D O I：

10.1002/jhet.5570380416

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of optically active derivatives of gamma -amino-butenoic acids and their cyclic derivatives, 2-amino-pyrrolin-4-ones, from alpha -amino acids is described. Partial racemization accompanies the formation of initial unsaturated gamma -amino- beta -hydroxy esters 5-8, as determined by chiral HPLC.

引用

页码：917 / 922

页数：6

共 21 条

[1] REACTIONS WITH DERIVATIVES OF GAMMA-CHLOROACETOACETIC ACID [J].

BOOSEN, KJ .

HELVETICA CHIMICA ACTA, 1977, 60 (04) :1256-1261

[2] KETO-ENOL TAUTOMERISM IN BETA DICARBONYLS STUDIED BY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY .1. PROTON CHEMICAL SHIFTS + EQUILIBRIUM CONSTANTS OF PURE COMPOUNDS [J].

BURDETT, JL ;

ROGERS, MT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (11) :2105-&

[3] Synthesis of N-alkoxycarbonyl-3-substituted tetramic acids and functionalized enols via C-acylation reactions of active methylene compounds with N-hydroxysuccinimide esters of N-alkoxycarbonyl-α-amino acids [J].

Detsi, A ;

Micha-Screttas, M ;

Igglessi-Markopoulou, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2443-2449

[4] Reactions of N-hydroxysuccinimide esters of N-alkoxycarbonyl-alpha-amino acids with active methylene compounds. Synthesis of 3-substituted tetramic acids [J].

Detsi, A ;

Markopoulos, J ;

IgglessiMarkopoulou, O .

CHEMICAL COMMUNICATIONS, 1996, (11) :1323-1324

[5]

DEWITT D, 1951, J AM CHEM SOC, P3359

[6]

Enders D, 1996, SYNTHESIS-STUTTGART, P941

[7] THE PREFERENTIAL DIRECTION OF ENOLIZATION OF SOME ASYMMETRIC 1,3-DICARBONYL COMPOUNDS IN SOLUTION - A STUDY BY MULTINUCLEAR NMR-SPECTROSCOPY [J].

GERALDES, CFGC ;

BARROS, MT ;

MAYCOCK, CD ;

SILVA, MI .

JOURNAL OF MOLECULAR STRUCTURE, 1990, 238 :335-346

[8] Synthesis, NMR spectroscopic and X-ray crystallographic studies of functionalized 2-aminopyrrolin-4-ones [J].

Gola, A ;

Samartzi, E ;

Bardakos, V ;

Petroliagi, M ;

Igglessi-Markopoulou, O ;

Markopoulos, J ;

Barkley, JV .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (04) :681-686

[9] A versatile approach to the activated form of (3S, 4R)-statine and its analogues [J].

Huang, PQ ;

Ye, JL ;

Chen, Z ;

Ruan, YP ;

Gao, JX .

SYNTHETIC COMMUNICATIONS, 1998, 28 (03) :417-426

[10]

LAKS JS, 1985, SYNTHESIS-STUTTGART, P291

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