A convenient synthesis of optically active phenylglycine

被引：15

作者：

Calmes, M ^{[1
]}

Daunis, J ^{[1
]}

Mai, N ^{[1
]}

Natt, F ^{[1
]}

机构：

[1] UNIV MONTPELLIER 2,LAB AMINOACIDES & PEPTIDES,CNRS,F-34095 MONTPELLIER 5,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 03期

关键词：

D O I：

10.1016/0040-4039(95)02170-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active R phenylglycine methyl ester hydrochloride (ee = 98%) was prepared in 90% yield from racemic phenylglycine. The key step was the base catalysed diastereoselective addition at -78 degrees C of R pantolactone to the N-phthalyl protected phenylglycine ketene

引用

页码：379 / 380

页数：2

共 8 条

[1] ASYMMETRIC-SYNTHESIS OF KETOPROFEN - A SURPRISING BASE CATALYST EFFECT DURING ASYMMETRIC ADDITION OF PANTOLACTONE TO METHYL (3-BENZOYLPHENYL) KETENE
CALMES, M
DAUNIS, J
JACQUIER, R
NATT, F
[J]. TETRAHEDRON, 1994, 50 (23) : 6875 - 6880
[2] (R)-3-HYDROXY-4,4-DIMETHYL-1-PHENYL-2-PYRROLIDINONE AND (S)-3-HYDROXY-4,4-DIMETHYL-1-PHENYL-2-PYRROLIDINONE, NEW CHIRAL AUXILIARIES FOR THE ASYMMETRIC-SYNTHESIS OF ALPHA-ARYLPROPANOIC ACIDS
CAMPS, P
GIMENEZ, S
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (04) : 991 - 1000
[3] LIGAND-EXCHANGE IN ASYMMETRIC REACTIONS OF LITHIUM ENOLATES - APPLICATION TO THE DERACEMIZATION OF ALPHA-AMINO-ACIDS
DUHAMEL, L
FOUQUAY, S
PLAQUEVENT, JC
[J]. TETRAHEDRON LETTERS, 1986, 27 (41) : 4975 - 4978
[4] SYNTHESIS OF AMINO-ACIDS AND PEPTIDES USING CHROMIUM CARBENE COMPLEX PHOTOCHEMISTRY
HEGEDUS, LS
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (07) : 299 - 305
[5] TIDWELL T, 1995, KETENES, P299
[6] SYNTHESIS OF OPTICALLY-ACTIVE ARYLGLYCINES BY PHOTOLYSIS OF OPTICALLY-ACTIVE (BETA-HYDROXYAMINO) CARBENE CHROMIUM (0) COMPLEXES
VERNIER, JM
HEGEDUS, LS
MILLER, DB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25) : 6914 - 6920
[7] WILLIAMS RM, 1989, ORGANIC CHEM SERIES, V7
[8] UBER ALPHA-PHTHALIMIDO-KETENE
WINTER, S
PRACEJUS, H
[J]. CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (01): : 151 - &

← 1 →