First synthesis of 3,3-difluoroserine and cysteine derivatives via Mg(0)-promoted selective C-F bond cleavage of trifluoromethylimines

被引：73

作者：

Mae, M ^{[1
]}

Amii, H ^{[1
]}

Uneyama, K ^{[1
]}

机构：

[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 41期

关键词：

amino acids; defluorination; enamines; imines;

D O I：

10.1016/S0040-4039(00)01350-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3,3-Difluoroserine and cysteine derivatives were synthesized via Mg(0)-promoted defluorination of trifluoromethylimines as a key step, followed by addition of alcohols and sulfenyl chloride, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7893 / 7896

页数：4

共 23 条

[1] Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes [J].

Amii, H ;

Kobayashi, T ;

Hatamoto, Y ;

Uneyama, K .

CHEMICAL COMMUNICATIONS, 1999, (14) :1323-1324

[2] POTENTIAL CARCINOSTATICS - SYNTHESIS AND BIOLOGICAL PROPERTIES OF D-DIFLOUROASPARTIC AND L-BETA,BETA-DIFLUOROASPARTIC ACID AND BETA,BETA-DIFLUOROASPARAGINE [J].

HAGEMAN, JJM ;

WANNER, MJ ;

KOOMEN, GJ ;

PANDIT, UK .

JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (12) :1677-1679

[3] THE SYNTHESIS OF DL-3,3-DIFLUOROGLUTAMIC ACID FROM A 3-OXOPROLINOL DERIVATIVE [J].

HART, BP ;

COWARD, JK .

TETRAHEDRON LETTERS, 1993, 34 (31) :4917-4920

[4] Highly stereoselective addition-elimination reaction of nucleophiles with ethyl 3,3-difluoro-2-[(trimethylsilyl)methyl]propenoate [J].

Huang, XH ;

He, PY ;

Shi, GQ .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :627-629

[5] REACTION OF 2,2-DIFLUOROVINYL KETONES WITH HETEROATOM NUCLEOPHILES - A GENERAL ONE-POT SYNTHESIS OF ALPHA-OXOKETENE ACETALS [J].

ICHIKAWA, J ;

KOBAYASHI, M ;

YOKOTA, N ;

NODA, Y ;

MINAMI, T .

TETRAHEDRON, 1994, 50 (40) :11637-11646

[6] MICHAEL ADDITION OF 2,2-DIFLUOROKETENE SILYL ACETAL - PREPARATION OF 4,4-DIFLUOROGLUTAMIC ACID AND 5,5-DIFLUOROLYSINE [J].

KITAGAWA, O ;

HASHIMOTO, A ;

KOBAYASHI, Y ;

TAGUCHI, T .

CHEMISTRY LETTERS, 1990, (08) :1307-1310

[7] SELECTIVE INHIBITORS OF BIOSYNTHESIS OF AMINERGIC NEUROTRANSMITTERS [J].

KOLLONITSCH, J ;

PATCHETT, AA ;

MARBURG, S ;

MAYCOCK, AL ;

PERKINS, LM ;

DOLDOURAS, GA ;

DUGGAN, DE ;

ASTER, SD .

NATURE, 1978, 274 (5674) :906-908

[8] FLUORODESULFURIZATION - NEW REACTION FOR FORMATION OF CARBON-FLUORINE BONDS [J].

KOLLONITSCH, J ;

MARBURG, S ;

PERKINS, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (19) :3107-3111

[9]

Kukhar VP., 1995, FLUORINE CONTAINING

[10] CATALYTIC IRREVERSIBLE INHIBITION OF MAMMALIAN ORNITHINE DECARBOXYLASE (E C 4 1 1 17) BY SUBSTRATE AND PRODUCT ANALOGS [J].

METCALF, BW ;

BEY, P ;

DANZIN, C ;

JUNG, MJ ;

CASARA, P ;

VEVERT, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (08) :2551-2553

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