Highly diastereoselective monoalkylation and Michael addition of N-(diphenylmethylene)glycinesultam under solid-liquid phase-transfer catalysis conditions using potassium carbonate as base

被引：30

作者：

López, A ^{[1
]}

Pleixats, R ^{[1
]}

机构：

[1] Univ Autonoma Barcelona, Dept Chem, E-08193 Barcelona, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(98)00169-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of a sultam-derived N-(diphenylmethylene)glycinate equivalent 1 with activated (allylic and propargylic) organic bromides and with Michael accepters under solid-liquid phase-transfer catalysis conditions, using potassium carbonate as base, affords the monoalkylated compounds with high diastereoselectivity (>97% d.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1967 / 1977

页数：11

共 40 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] ASYMMETRIC ALKYLATION OF 8-PHENYLMENTHYL N-[BIS(METHYLTHIO)METHYLENE]GLYCINATE ENOLATES - SYNTHESIS OF D-ALPHA-AMINO AND L-ALPHA-AMINO ACIDS FROM A SINGLE CHIRAL PRECURSOR [J].

ALVAREZIBARRA, C ;

CSAKY, AG ;

MAROTO, R ;

QUIROGA, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7934-7940

[3] SYNTHESIS, RESOLUTION AND ABSOLUTE-CONFIGURATION DETERMINATION OF (S)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND (R)-4-FORMYL-5-HYDROXY[2.2]PARACYCLOPHANE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

ANTONOV, DY ;

BELOKON, YN ;

IKONNIKOV, NS ;

ORLOVA, SA ;

PISAREVSKY, AP ;

RAEVSKI, NI ;

ROZENBERG, VI ;

SERGEEVA, EV ;

STRUCHKOV, YT ;

TARAROV, VI ;

VORONTSOV, EV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (14) :1873-1879

[4] DIASTEREOSELECTIVE ALKYLATION OF SULTAM-DERIVED AMINO-ACID ALDIMINES PREPARATION OF C-ALPHA-METHYLATED AMINO-ACIDS [J].

AYOUB, M ;

CHASSAING, G ;

LOFFET, A ;

LAVIELLE, S .

TETRAHEDRON LETTERS, 1995, 36 (23) :4069-4072

[5] PEPTIDE-SYNTHESIS IN AQUEOUS-SOLUTION .4. PREPARATION AND PROPERTIES OF [PARA-(BENZYLOXYCARBONYLOXY)PHENYL]DIMETHYLSULFONIUM METHYL SULFATE (Z-ODSP), [PARA-(TERT-BUTOXYCARBONYLOXY)PHENYL]DIMETHYLSULFONIUM METHYL SULFATE (BOC-ODSP) AND [PARA-(9-FLUORENYLMETHYLOXYCARBONYLOXY)PHENYL]DIMETHYLSULFONIUM METHYL SULFATE (FMOC-ODSP) AS WATER-SOLUBLE NORMAL-ACYLATING REAGENTSL [J].

AZUSE, I ;

TAMURA, M ;

KINOMURA, K ;

OKAI, H ;

KOUGE, K ;

HAMATSU, F ;

KOIZUMI, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (10) :3103-3108

[6] NUCLEOPHILIC RING-OPENING OF AZIRIDINE-2-CARBOXYLATES WITH WITTIG REAGENTS - AN ENANTIOEFFICIENT SYNTHESIS OF UNSATURATED AMINO-ACIDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

ROBINSON, NG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (03) :153-155

[7] SYNTHESIS OF ENANTIO-ISOMERICALLY AND DIASTEREO-ISOMERICALLY PURE BETA-SUBSTITUTED AND GAMMA-SUBSTITUTED GLUTAMIC ACIDS VIA GLYCINE CONDENSATION WITH ACTIVATED OLEFINS [J].

BELOKON, YN ;

BULYCHEV, AG ;

RYZHOV, MG ;

VITT, SV ;

BATSANOV, AS ;

STRUCHKOV, YT ;

BAKHMUTOV, VI ;

BELIKOV, VM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1865-1872

[8] L-(6,7-dimethoxy-4-coumaryl) alanine: an intrinsic probe for the labelling of peptides [J].

Bennett, FA ;

Barlow, DJ ;

Dodoo, ANO ;

Hider, RC ;

Lansley, AB ;

Lawrence, MJ ;

Marriott, C ;

Bansal, SS .

TETRAHEDRON LETTERS, 1997, 38 (42) :7449-7452

[9] Asymmetric synthesis of alpha-methyl alpha-amino acids by diastereoselective alkylation of optically active 6-isopropyl-3-methyl-2,3-dihydro-6H-1,4-oxazin-2-ones [J].

Chinchilla, R ;

Falvello, LR ;

Galindo, N ;

Najera, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (09) :995-997

[10] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].

Corey, EJ ;

Xu, F ;

Noe, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415

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