A new synthesis of α-amino acid derivatives by reaction of N-acyl-α-triphenylphosphonioglycinates with carbon nucleophiles

被引：7

作者：

Mazurkiewicz, R ^{[1
]}

Grymel, M ^{[1
]}

机构：

[1] Silesian Tech Univ, Inst Organ Chem & Technol, PL-44100 Gliwice, Poland

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2000年 / 164卷

关键词：

alpha-triphenylphosphonioglycinates; cationic glycine equivalent; carbon nucleophiles; nucleophilic substitution; glycine alpha-functionalization;

D O I：

10.1080/10426500008045231

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Recently described(1), easily accessible N-acyl-alpha -triphenylphosphonioglycinates react smoothly with activated carbonyl compounds or enamines in the presence of a base (DBU or Et3N) yielding the corresponding alpha -functionaIized glycine derivatives.

引用

页码：33 / 43

页数：11

共 21 条

[1] ZINC MEDIATED ADDITION OF ACTIVE HALIDES TO A GLYCINE CATION EQUIVALENT - SYNTHESIS OF N-BOC-L-PROPARGYLGLYCINE [J].

ABOOD, NA ;

NOSAL, R .

TETRAHEDRON LETTERS, 1994, 35 (22) :3669-3672

[2]

[Anonymous], 1992, ALDRICHIM ACTA

[3] CONVERSION OF SERINE AND THREONINE RESIDUES INTO ALPHA-ACYLOXY-HALOGENOGLYCINE, ALPHA-ALKYLTHIO-HALOGENOGLYCINE, AND ALPHA-HALOGENOGLYCINE MOIETIES - A NEW STRATEGY FOR THE MODIFICATION OF PEPTIDES [J].

APITZ, G ;

STEGLICH, W .

TETRAHEDRON LETTERS, 1991, 32 (27) :3163-3166

[4] NEW SYNTHESES OF ALPHA-AMINO-ACIDS BASED ON N-ACYLIMINO ACETATES [J].

BRETSCHNEIDER, T ;

MILTZ, W ;

MUNSTER, P ;

STEGLICH, W .

TETRAHEDRON, 1988, 44 (17) :5403-5414

[5] PTC and organic bases LiCl assisted alkylation of imidazolidinone-glycine iminic derivatives for the asymmetric synthesis of α-amino acids [J].

Guillena, G ;

Nájera, C .

TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3935-3938

[6] REACTION OF ACYLAMINOBROMOMALONATES AND ACYLAMINOBROMOACETATES WITH TRIALKYLPHOSPHITES - A SIMPLE SYNTHESIS OF ETHYL 2-AMINO-2-(DIETHOXYPHOSPHORYL)ACETATE [J].

KOBER, R ;

STEGLICH, W .

LIEBIGS ANNALEN DER CHEMIE, 1983, (04) :599-609

[7] REACTION OF ACYLIMINOMALONIC ESTERS WITH C-NUCLEOPHILES, AN UMPOLUNG IN THE ACYLAMINOMALONIC ESTER SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

KOBER, R ;

HAMMES, W ;

STEGLICH, W .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (03) :203-204

[8] SYNTHESIS OF DIASTEREO- AND ENANTIOMERICALLY PURE ALPHA-AMINO-GAMMA-OXO ACID ESTERS BY REACTION OF ACYLIMINOACETATES WITH ENAMINES DERIVED FROM 6-MEMBERED KETONES [J].

KOBER, R ;

PAPADOPOULOS, K ;

MILTZ, W ;

ENDERS, D ;

STEGLICH, W ;

REUTER, H ;

PUFF, H .

TETRAHEDRON, 1985, 41 (09) :1693-1701

[9] N-Acyl-a-triphenylphosphonioglycinates:A Novel Cationic Glycine Equivalent and its Reactions with Heteroatom NucleophilesN-Acyl-α-triphenylphosphonionoglycinate: Ein neues kationisches Glycinäquivalent und seineReaktionen mit Heteroatomnucleophilen [J].

Roman Mazurkiewicz ;

Mirosława Grymel .

Monatshefte für Chemie / Chemical Monthly, 1999, 130 (4) :597-604

[10] Chiral auxiliaries with a switching center:: New tools in asymmetric synthesis.: Application to the synthesis of enantiomerically pure (R)- and (S)-α-amino acids [J].

Meyer, L ;

Poirier, JM ;

Duhamel, P ;

Duhamel, L .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8094-8095

← 1 2 3 →