A NOVEL METHOD FOR THE SYNTHESIS OF ALPHA-FLUOROKETONES VIA CLAISEN REARRANGEMENT

被引：12

作者：

REUTRAKUL, V

KRUAHONG, T

POHMAKOTR, M

机构：

[1] Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, 10400

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)76986-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorine-facilitated Claisen rearrangement has been employed as a key step in the synthesis of alpha-fluoroketones 5. The elimination of sulfenic acid from the allyl ethers 3 are effected under FVP conditions.

引用

页码：4853 / 4856

页数：4

共 21 条

[1]

ARAKI K, 1993, TETRAHEDRON LETT, V32, P2251

[2] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS [J].

BLECHERT, S .

SYNTHESIS-STUTTGART, 1989, (02) :71-82

[3]

BUECHI G, 1983, J ORG CHEM, V48, P5406

[4] ON THE COHERENCE OF INCORPORATION OF THE FLUOROVINYL MOIETY INTO BIOACTIVE ORGANIC-COMPOUNDS - SYNTHESIS OF AN INSECT JUVENILE HORMONE-III FLUORINATED ANALOG [J].

CAMPS, F ;

MESSEGUER, A ;

SANCHEZ, FJ .

TETRAHEDRON, 1988, 44 (16) :5161-5167

[5] FLUORINE-CONTAINING ORGANOZINC REAGENTS .4. THE REFORMATSKII-CLAISEN REACTION OF CHLORODIFLUOROACETIC ACID-DERIVATIVES [J].

GREUTER, H ;

LANG, RW ;

ROMANN, AJ .

TETRAHEDRON LETTERS, 1988, 29 (27) :3291-3294

[6]

Hill R. K., 1984, ASYMMETRIC SYNTHESIS, V3B

[7] STEREOCHEMICAL CONTROL IN THE ESTER ENOLATE CLAISEN REARRANGEMENT .1. STEREOSELECTIVITY IN SILYL KETENE ACETAL FORMATION [J].

IRELAND, RE ;

WIPF, P ;

ARMSTRONG, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :650-657

[8]

KOLB M, 1988, SYNTHESIS-STUTTGART, P469

[9] PREPARATION AND REARRANGEMENT OF 2-ALLYLOXYETHYL ARYL SULFOXIDES - A MERCURY-FREE CLAISEN SEQUENCE [J].

MANDAI, T ;

UEDA, M ;

HASEGAWA, S ;

KAWADA, M ;

TSUJI, J ;

SAITO, S .

TETRAHEDRON LETTERS, 1990, 31 (28) :4041-4044

[10]

METCALF BM, 1985, TETRAHEDRON LETT, V24, P2861

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