FRIEDEL-CRAFTS ALPHA-AMINOACYLATION OF ALKYLBENZENE WITH A CHIRAL N-CARBOXY-ALPHA-AMINO ACID ANHYDRIDE WITHOUT LOSS OF CHIRALITY

被引：22

作者：

ITOH, O

HONNAMI, T

AMANO, A

MURATA, K

KOICHI, Y

SUGITA, T

机构：

[1] Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University, Kyoto 606, Sakyo-ku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 26期

关键词：

D O I：

10.1021/jo00052a059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Friedel-Crafts-type alpha-aminoacylation of alkylbenzene with N-carboxy anhydrides Of five L-alpha-amino acids was developed. Five new alpha-aminoalkyl p-methylphenyl ketones and other alpha-aminoalkyl aryl ketones were obtained and isolated as free bases or hydrochloride salts. The chiralities of the original L-alpha-amino acids were retained during this acylation.

引用

页码：7334 / 7338

页数：5

共 12 条

[1] ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - AMINO ACYLATION WITH N-ACYLAMINO ACIDS
BUCKLEY, TF
RAPOPORT, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) : 6157 - 6163
[2] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES
DALE, JA
DULL, DL
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) : 2543 - &
[3] THE PREPARATION OF N-CARBOXYANHYDRIDES OF ALPHA-AMINO-ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE
DALY, WH
POCHE, D
[J]. TETRAHEDRON LETTERS, 1988, 29 (46) : 5859 - 5862
[4] On N-carbonic acid-anhydride.
Fuchs, F
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1922, 55 : 2943 - 2943
[5] CONTROLLED SYNTHESIS OF PEPTIDES IN AQUEOUS MEDIUM .8. PREPARATION AND USE OF NOVEL ALPHA-AMINO ACID N-CARBOXYANHYDRIDES
HIRSCHMANN, R
SCHWAM, H
STRACHAN, RG
SCHOENEWALDT, EF
BARKEMEYER, H
MILLER, SM
CONN, JB
GARSKY, V
VEBER, DF
DENKEWALTER, RG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (11) : 2746 - +
[6] ISHAI DB, 1952, J AM CHEM SOC, V74, P3688
[7] Glycine-carbonic acid.
Leuchs, H
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1906, 39 : 857 - 861
[8] MCCLURE DE, 1985, J ORG CHEM, V46, P2431
[9] PEPTIDE SYNTHESIS VIA N-ACYLATED AZIRIDINONE .2. REACTION OF N-ACYLATED AZIRIDINONE AND ITS USE IN PEPTIDE SYNTHESIS
MIYOSHI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (05) : 1489 - 1496
[10] N-(TRIFLUOROACETYL)-ALPHA-AMINO ACID-CHLORIDES AS CHIRAL REAGENTS FOR FRIEDEL-CRAFTS SYNTHESIS
NORDLANDER, JE
NJOROGE, FG
PAYNE, MJ
WARMAN, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) : 3481 - 3484

← 1 2 →