Enantioselective allylation of alpha-ketoester oximes with an external chiral ligand: Asymmetric synthesis of allylglycines and allylalanine

被引：64

作者：

Hanessian, S

Yang, RY

机构：

[1] Department of Chemistry, Univ. de Montréal, Montréal, Que. H3C 3J7, C.P. 6128, Succ. Centre-ville

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)02112-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly enantioselective allylation of oximes of alpha-ketoesters is described with phenyl substituted chiral bis(oxazoline) as external ligand of allylzinc reagents. This method provides an efficient and convenient access to N-benzyloxy allylglycine, allylglycine and chain substituted variants with high enantiomeric purities. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：8997 / 9000

页数：4

相关论文

共 38 条

[1] 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

[2] ENANTIOMERICALLY ENRICHED ALPHA-METHYL AMINO-ACIDS - USE OF AN ACYCLIC, CHIRAL ALANINE-DERIVED DIANION WITH A HIGH DIASTEREOFACIAL BIAS [J].

BERKOWITZ, DB ;

SMITH, MK .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1233-1238

[3] SYNTHESIS OF (OPTICALLY-ACTIVE) SULFUR-CONTAINING TRIFUNCTIONAL AMINO-ACIDS BY RADICAL-ADDITION TO (OPTICALLY-ACTIVE) UNSATURATED AMINO-ACIDS [J].

BROXTERMAN, QB ;

KAPTEIN, B ;

KAMPHUIS, J ;

SCHOEMAKER, HE .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6286-6294

[4] 1,3-AMINOALCOHOLS BY REDUCTIVE CLEAVAGE OF ISOXAZOLIDINES WITH MOLYBDENUM HEXACARBONYL [J].

CICCHI, S ;

GOTI, A ;

BRANDI, A ;

GUARNA, A ;

DESARLO, F .

TETRAHEDRON LETTERS, 1990, 31 (23) :3351-3354

[5] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].

COREY, EJ ;

IMAI, N ;

ZHANG, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729

[6] Hydroboration of vinylglycine and allylglycine as a route to boron-derivatives of alpha-amino acids. [J].

Denniel, V ;

Bauchat, P ;

Danion, D ;

DanionBougot, R .

TETRAHEDRON LETTERS, 1996, 37 (29) :5111-5114

[7] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS [J].

EVANS, DA ;

WOERPEL, KA ;

HINMAN, MM ;

FAUL, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :726-728

[8] SYNTHESIS OF MODIFIED PARTIAL STRUCTURES OF THE BACTERIAL-CELL WALL .2. RETARDED METABOLISM OF LIPOPEPTIDES BY INSERTION OF ALPHA-SUBSTITUTED ALPHA-AMINO-ACIDS [J].

FRAUER, A ;

MEHLFUHRER, M ;

THIRRING, K ;

BERNER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4215-4222

[9] Highly selective asymmetric synthesis of homoallylic amines with and without a beta-substituent by the reaction of allylic titanium compounds with chiral imines [J].

Gao, YA ;

Sato, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8136-8137

[10]

HAMON DPG, 1991, J CHEM SOC CHEM COMM, P772

← 1 2 3 4 →