HIGHLY STEREOSELECTIVE RADICAL-ADDITION TO A TRISUBSTITUTED ALKENE BY LOW-TEMPERATURE PHOTOLYSIS OF THIOHYDROXAMIC ESTERS

被引：34

作者：

SCOTT, DM ^{[1
]}

MCPHAIL, AT ^{[1
]}

PORTER, NA ^{[1
]}

机构：

[1] DUKE UNIV,PAUL M GROSS CHEM LAB,DEPT CHEM,DURHAM,NC 27706

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 12期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)88852-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Low temperature carbon radical addition to α,β-unsaturated amides of trans-2,5-dimethylpyrrolidine was achieved in high yield with high diastereoselectivity by photolysis of Barton esters. Use of an olefin substituted with three electron withdrawing groups provides synthetic versatility and regiospecificity. © 1990.

引用

页码：1679 / 1682

页数：4

共 10 条

[1] THE INVENTION OF RADICAL REACTIONS .15. SOME MECHANISTIC ASPECTS OF THE DECARBOXYLATIVE REARRANGEMENT OF THIOHYDROXAMIC ESTERS [J].

BARTON, DHR ;

BRIDON, D ;

FERNANDEZPICOT, I ;

ZARD, SZ .

TETRAHEDRON, 1987, 43 (12) :2733-2740

[2]

EVANS DA, 1984, ASYMMETRIC SYNTHESIS, P2

[3] SYNTHESES WITH RADICALS-C-C BOND FORMATION VIA ORGANOTIN AND ORGANOMERCURY COMPOUNDS [J].

GIESE, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (07) :553-565

[4] ELECTRON-DEFICIENT TRISUBSTITUTED OLEFINS - NEW CLASS OF REACTIVE COMONOMERS [J].

HALL, HK ;

DALY, RC .

MACROMOLECULES, 1975, 8 (01) :22-31

[5]

HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111

[6]

KELLY TR, 1973, TETRAHEDRON LETT, V6, P437

[7]

KRAPCHO AP, 1973, TETRAHEDRON LETT, V12, P957

[8]

LUTOMSKI KA, 1984, ASYMMETRIC SYNTHESIS, V3, P213

[9] RADICAL-ADDITION TO AMIDE-SUBSTITUTED ALKENES - STEREOSELECTIVE INTERMOLECULAR RADICAL ADDITIONS [J].

PORTER, NA ;

SCOTT, DM ;

LACHER, B ;

GIESE, B ;

ZEITZ, HG ;

LINDNER, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8311-8312

[10] ASYMMETRIC INDUCTION .2. ENANTIOSELECTIVE ALKYLATION OF CYCLOHEXANONE VIA A CHIRAL ENAMINE [J].

WHITESELL, JK ;

FELMAN, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (09) :1663-1664

← 1 →