STEREOSELECTIVE SYNTHESIS OF DISUBSTITUTED AND TRISUBSTITUTED ALKENES VIA INTERMOLECULAR ADDITION OF VINYL RADICALS TO ALKENES

被引：13

作者：

MIURA, K ^{[1
]}

ITOH, D ^{[1
]}

HONDO, T ^{[1
]}

HOSOMI, A ^{[1
]}

机构：

[1] UNIV TSUKUBA,DEPT CHEM,TSUKUBA,IBARAKI 305,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 51期

关键词：

D O I：

10.1016/0040-4039(94)88522-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vinyl radicals, generated from the reaction of vinyl iodides with tributylstannyl radical, react with electron-deficient alkenes to give di- or trisubstituted alkenes in moderate to good yields. The stereoselectivity is largely dependent on the substituent at 1- and 2-position of vinyl iodides.

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页码：9605 / 9608

页数：4

相关论文

共 22 条

[1] FREE-RADICAL CYCLIZATION APPROACH TO THE SOUTHERN MOIETY OF AVERMECTINS [J].

ARDISSON, J ;

FEREZOU, JP ;

JULIA, M ;

PANCRAZI, A .

TETRAHEDRON LETTERS, 1987, 28 (18) :2001-2004

[2]

Curran D. P., 1991, COMPREHENSIVE ORGANI, V4, P715

[3] RADICAL TRANSLOCATION REACTIONS OF VINYL RADICALS - SUBSTITUENT EFFECTS ON 1,5-HYDROGEN-TRANSFER REACTIONS [J].

CURRAN, DP ;

SHEN, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) :6051-6059

[4] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1. [J].

CURRAN, DP .

SYNTHESIS-STUTTGART, 1988, (06) :417-439

[5] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES [J].

CURRAN, DP ;

CHANG, CT .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3140-3157

[6] THE SCOPE OF RADICAL CC-COUPLING BY THE TIN METHOD [J].

GIESE, B ;

GONZALEZGOMEZ, JA ;

WITZEL, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01) :69-70

[7] INFLUENCE OF H-DONOR AND TEMPERATURE ON THE STEREOSELECTIVITY OF RADICAL REACTIONS [J].

GIESE, B ;

GONZALEZGOMEZ, JA ;

LACHHEIN, S ;

METZGER, JO .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1987, 26 (05) :479-480

[8]

GIESE B, 1989, TETRAHEDRON LETT, V30, P381

[9]

Giese B., 1986, RADICALS ORGANIC SYN

[10] PERSISTENT CARBON-CENTERED RADICALS [J].

GRILLER, D ;

INGOLD, KU .

ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (01) :13-19