A VERSATILE ENTRY INTO THE SYNTHESIS OF ALPHA-(MONOFLUOROMETHYL) AMINO-ACIDS - PREPARATION OF ALPHA-(MONOFLUOROMETHYL) SERINE AND (E)-DEHYDRO-ALPHA-(MONOFLUOROMETHYL) ORNITHINE

被引：8

作者：

VANHIJFTE, L

HEYDT, V

KOLB, M

机构：

[1] Marion Merrell Dow Research Institute Strasbourg Research Center, 67009 Strasbourg Cedex

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)74090-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new entry to the synthesis of alpha-(monofluoromethyl) amino acids is described. The synthesis is based on a Strecker reaction on an alpha-(monofluoromethyl) ketone. As an example, alpha-(monofluoromethyl) serine was synthesized and used as starting material for a new synthesis of (E)-dehydro-alpha-(monofluromethyl ornithine.

引用

页码：4793 / 4796

页数：4

共 33 条

[11] KINETICS OF THE CARBOXYPEPTIDASE A-CATALYZED HYDROLYSIS OF ALPHA-(BENZOYLAMINO)CINNAMOYL DERIVATIVES OF VARIOUS AMINO-ACIDS
SUH, JH
CHO, MH
BIOORGANIC CHEMISTRY, 1990, 18 (03) : 276 - 282
[12] DEHYDRO AMINO-ACIDS .9. FACILE SYNTHESIS OF ALPHA,BETA-DEHYDRO AMINO-ACID ESTERS
SCHMIDT, U
OHLER, E
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (05): : 327 - 328
[13] Palladium-catalysed asymmetric allylic substitution: Synthesis of alpha- and beta-amino acids
Bower, JF
Jumnah, R
Williams, AC
Williams, JMJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (09): : 1411 - 1420
[14] REACTION OF GUANIDINE DERIVATIVES WITH FORMALDEHYDE AND AMINO-ACIDS .1. REACTION OF AMINOGUANIDINE DERIVATIVES OF ALPHA-(TRIHALOMETHYL)AMINES WITH CH2O AND ALPHA-AMINO-ACIDS
LUKASIEWICZ, A
ROCZNIKI CHEMII, 1975, 49 (05): : 935 - 943
[15] SYNTHESIS OF ASYMMETRIC (E)-ALPHA-[2-PHENYL(ETHYL)CYCLOPROPYL]GLYCINES FROM SERINE BY DIASTEREOSELECTIVE DIBROMOCYCLOPROPANATION
DEFRUTOS, MP
FERNANDEZ, MD
FERNANDEZALVAREZ, E
BERNABE, M
TETRAHEDRON, 1992, 48 (06) : 1123 - 1130
[16] A REAGENT FOR THE EFFICIENT CLEAVAGE OF N-BENZOYLHOMOSERINE LACTONES - ACCESS TO ALPHA-(2-PHENYLSELENO)ETHYL AMINO-ACIDS
PEDERSEN, ML
BERKOWITZ, DB
TETRAHEDRON LETTERS, 1992, 33 (48) : 7315 - 7318
[17] Synthesis of quaternary amino acids bearing an alpha-(2′Z)-fluorovinyl branch:: Potential PLP enzyme inactivators.
Berkowitz, DB
de la Salud-Bea, R
Jahng, WJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U156 - U156
[18] ENANTIOSPECIFIC SYNTHESIS OF AMINO-ACIDS - PREPARATION OF (R)-ALPHA-METHYLASPARTIC AND (S)-ALPHA-METHYLASPARTIC ACID FROM (S)-TRYPTOPHAN
CHAN, CO
CRICH, D
NATARAJAN, S
TETRAHEDRON LETTERS, 1992, 33 (24) : 3405 - 3408
[19] PREPARATION OF ALPHA-(N-TRIMETHYLSILYL)IMINO ESTERS AND THEIR USE IN THE SYNTHESIS OF ALPHA-AMINO ESTERS AND 2-ALKOXYCARBONYLIMIDAZOL-4(2H)-ONES
MATSUDA, Y
TANIMOTO, S
OKAMOTO, T
ALI, SM
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (02): : 279 - 281
[20] CYTO-ACTIVE AMINO-ACIDS AND PEPTIDES .4. SYNTHESIS OF ALPHA-[P-DI-(2-CHLOROETHYL)AMINO-BENZYLIDENE AND BENZYL-]HIPPURAMIDES AND HIPPURAMIDO-ACIDS
BERGEL, F
STOCK, JA
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (NOV): : 4563 - 4567

← 1 2 3 4 →