AN APPLICATION OF THE TROST REACTION TO THE STEREOSELECTIVE SYNTHESIS OF TRANSTETRASUBSTITUTED FLUOROALKENES

被引：15

作者：

FISH, PV ^{[1
]}

REDDY, SP ^{[1
]}

LEE, CH ^{[1
]}

JOHNSON, WS ^{[1
]}

机构：

[1] STANFORD UNIV,DEPT CHEM,STANFORD,CA 94305

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)74700-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The coupling of beta-fluoroallylic acetates (1) with stabilised ester-enolates (3), in the presence of catalytic palladium(0), gave tetrasubstituted fluoroalkenes (2) in good yield and with generally satisfactory trans-stereoselectivity.

引用

页码：8001 / 8004

页数：4

共 17 条

[1] SYNTHESES OF ORGANOFLUORINE COMPOUNDS .8. SOLVOLYTIC RING-OPENING OF ALKOXYCHLOROFLUOROCYCLOPROPANES - READY ACCESS TO FLUORINATED ALPHA-BETA-UNSATURATED ALDEHYDES AND KETONES [J].

BESSIERE, Y ;

SAVARY, DNH ;

SCHLOSSER, M .

HELVETICA CHIMICA ACTA, 1977, 60 (05) :1739-1746

[2] STEREOSPECIFIC PREPARATION OF (Z)-ISOMERS AND (E)-ISOMERS, RESPECTIVELY, OF SOME VINYL FLUORIDES [J].

BOCHE, G ;

FAHRMANN, U .

CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (12) :4005-4009

[3] ALPHA-FLUOROMETHYL-N-METHYL-PHENYLSULPHOXIMINE - A NEW FLUOROMETHYLENATION REAGENT [J].

BOYS, ML ;

COLLINGTON, EW ;

FINCH, H ;

SWANSON, S ;

WHITEHEAD, JF .

TETRAHEDRON LETTERS, 1988, 29 (27) :3365-3368

[4] A HIGHLY STEREOSELECTIVE SYNTHESIS OF TRANS-TRISUBSTITUTED OLEFINIC BONDS [J].

BRADY, SF ;

ILTON, MA ;

JOHNSON, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (11) :2882-+

[5] SURPRISING STEREOCHEMICAL CONTROL OF WITTIG OLEFINATION INVOLVING REACTION OF FLUORINE-CONTAINING PHOSPHORANIUM SALT AND ALDEHYDES [J].

COX, DG ;

GURUSAMY, N ;

BURTON, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (09) :2811-2812

[6]

EMSLEY JW, 1977, FLUORINE COUPLING CO, P187

[7] CLAISEN REARRANGEMENT OF ALLYL ESTERS [J].

IRELAND, RE ;

MUELLER, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (16) :5897-&

[8] A SIMPLE STEREOSELECTIVE VERSION OF CLAISEN REARRANGEMENT LEADING TO TRANS-TRISUBSTITUTED OLEFINIC BONDS . SYNTHESIS OF SQUALENE [J].

JOHNSON, WS ;

WERTHEMANN, L ;

BARTLETT, WR ;

BROCKSOM, TJ ;

LI, TT ;

FAULKNER, DJ ;

PETERSEN, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) :741-+

[9]

JOHNSON WTG, IN PRESS J AM CHEM S

[10] STEREOSPECIFIC SYNTHESIS OF ALKENYL FLUORIDES (WITH RETENTION) VIA ORGANOMETALLIC INTERMEDIATES [J].

LEE, SH ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (09) :2445-2447

← 1 2 →