Ethyl N-(diphenylmethylene)glycinate as anionic glycine equivalent. Monoalkylation, dialkylation and Michael additions under solid-liquid phase-transfer catalysis.

被引：37

作者：

Lopez, A

MorenoManas, M

Pleixats, R

Roglans, A

Ezquerra, J

Pedregal, C

机构：

[1] UNIV AUTONOMA BARCELONA,DEPT CHEM,E-08193 BARCELONA,SPAIN

[2] CTR INVEST LILLY,E-28130 MADRID,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 24期

关键词：

D O I：

10.1016/0040-4020(96)00395-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl N-(diphenylmethylene)glycinate, 1, undergoes monoalkylations, dialkylations and Michael additions to ethylenic and acetylenic accepters under appropriate solid-liquid phase transfer catalysis conditions. Further transformations of the alpha-disubstituted ketimines lead to alpha-alkylated aspartic and glutamic acid derivatives 10, 15, 19 and 26, to bicyclic amino, acids or denrivatives featuring pyrazolone and isoxazolone moieties 30 and 33, and to alpha-substituted (h)-3,4-dehydroglutamic acids. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：8365 / 8386

页数：22

共 85 条

[1] OVERALL ENANTIOSELECTIVE ALPHA-ALKYLATION OF ASPARTIC AND GLUTAMIC-ACID THROUGH DILITHIUM ENOLATOCARBOXYLATES OF 2-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]ACETIC AND 3-[3-BENZOYL-2-(TERT-BUTYL)-1-METHYL-5-OXOIMIDAZOLIDIN-4-YL]PROPIONIC ACID, RESPECTIVELY
AEBI, JD
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1985, 68 (06) : 1507 - 1518
[2] SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED CYCLIC ALPHA-AMINO-ACIDS STRUCTURALLY RELATED TO ACPD
ALONSO, F
MICO, I
NAJERA, C
SANSANO, JM
YUS, M
EZQUERRA, J
YRURETAGOYENA, B
GRACIA, I
[J]. TETRAHEDRON, 1995, 51 (37) : 10259 - 10280
[3] VERSATILE STEREOSELECTIVE SYNTHESIS OF COMPLETELY PROTECTED TRIFUNCTIONAL ALPHA-METHYLATED ALPHA-AMINO-ACIDS STARTING FROM ALANINE
ALTMANN, E
NEBEL, K
MUTTER, M
[J]. HELVETICA CHIMICA ACTA, 1991, 74 (04) : 800 - 806
[4] DIASTEREOSELECTIVE SYNTHESIS OF SUBSTITUTED GLUTAMIC-ACID DERIVATIVES VIA MICHAEL ADDITIONS OF N-[BIS(METHYLTHIO)METHYLENE]GLYCINATES UNDER SOLID-LIQUID PHASE-TRANSFER CATALYSIS
ALVAREZIBARRA, C
CSAKY, AG
MAROTO, M
QUIROGA, ML
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6700 - 6705
[5] BEGTRUP M, 1993, SYNTHESIS-STUTTGART, P861
[6] SYNTHESIS OF POTENTIAL AGONISTS AND ANTAGONISTS FOR CENTRAL GLUTAMATE RECEPTORS BY A NOVEL RING SWITCHING PROCESS
BOWLER, AN
DOYLE, PM
YOUNG, DW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (05) : 314 - 316
[7] 2-CARBOXYTETRAHYDROQUINOLINES - CONFORMATIONAL AND STEREOCHEMICAL REQUIREMENTS FOR ANTAGONISM OF THE GLYCINE SITE ON THE NMDA RECEPTOR
CARLING, RW
LEESON, PD
MOSELEY, AM
BAKER, R
FOSTER, AC
GRIMWOOD, S
KEMP, JA
MARSHALL, GR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) : 1942 - 1953
[8] REACTIONS OF FLUOROBENZENE TRICARBONYLCHROMIUM COMPLEXES WITH ANIONS FROM SCHIFF-BASES OF ALPHA-AMINO ESTERS - ENANTIOSELECTIVE SYNTHESIS OF ALPHA-ARYL AMINO-ACIDS
CHAARI, M
JENHI, A
LAVERGNE, JP
VIALLEFONT, P
[J]. TETRAHEDRON, 1991, 47 (26) : 4619 - 4630
[9] ENANTIOSPECIFIC SYNTHESIS OF AMINO-ACIDS - PREPARATION OF (R)-ALPHA-METHYLASPARTIC AND (S)-ALPHA-METHYLASPARTIC ACID FROM (S)-TRYPTOPHAN
CHAN, CO
CRICH, D
NATARAJAN, S
[J]. TETRAHEDRON LETTERS, 1992, 33 (24) : 3405 - 3408
[10] EXCITATORY AMINO-ACID RECEPTOR LIGANDS - SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 3-ISOXAZOLOL AMINO-ACIDS STRUCTURALLY RELATED TO HOMOIBOTENIC ACID
CHRISTENSEN, IT
EBERT, B
MADSEN, U
NIELSEN, B
BREHM, L
KROGSGAARDLARSEN, P
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (19) : 3512 - 3519

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