HIGHLY DIASTEREOSELECTIVE FORMATION OF SUBSTITUTED INDOLIZIDINES AND QUINOLIZIDINES BY RADICAL CYCLIZATION

被引：65

作者：

BECKWITH, ALJ

JOSEPH, SP

MAYADUNNE, RTA

机构：

[1] Research School of Chemistry, Australian National University, Canberra

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Substituted 2,3-dihydro-4-pyridinones (eg., 1a) bearing an (omega-bromoacyl)-, (o-bromoaroyl)-, or (o-bromophenyl)aeetyl group on nitrogen, when treated with tributylstannane, undergo highly diastereoselective cyclization by intramolecular homolytic addition anti to the substituent at C-2; molecular mechanics calculation support the view that the diastereoselectivity arises from the nonbonded interaction between the substituent and the amide carbonyl group.

引用

页码：4198 / 4199

页数：2

共 23 条

[1] ARIPOVSKII AV, 1989, RUSS J PHYS CHEM, V63, P754
[2] FORMATION OF SOME BICYCLIC SYSTEMS BY RADICAL RING-CLOSURE
BECKWITH, ALJ
PHILLIPOU, G
SERELIS, AK
[J]. TETRAHEDRON LETTERS, 1981, 22 (29) : 2811 - 2814
[3] THE SYNTHESIS OF INDOLIZIDINE AND QUINOLIZIDINE RING-SYSTEMS BY FREE-RADICAL CYCLIZATION OF 4-AZA-6-METHOXYCARBONYL-5-HEXENYL RADICALS
BECKWITH, ALJ
WESTWOOD, SW
[J]. TETRAHEDRON, 1989, 45 (16) : 5269 - 5282
[4] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY
BECKWITH, ALJ
SCHIESSER, CH
[J]. TETRAHEDRON, 1985, 41 (19) : 3925 - 3941
[5] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS
BECKWITH, ALJ
[J]. TETRAHEDRON, 1981, 37 (18) : 3073 - 3100
[6] A HIGHLY STEREOCONTROLLED, 4-STEP SYNTHESIS OF (+/-)-LASUBINE-II
BROWN, JD
FOLEY, MA
COMINS, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) : 7445 - 7447
[7] SHORT SYNTHESIS OF (+/-)-5-(3-FURYL)OCTAHYDRO-8-METHYLINDOLIZINES, ALKALOIDS RELATED TO A COMPONENT OF CASTOREUM - USE OF RADICAL CYCLIZATION
CLIVE, DLJ
BERGSTRA, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) : 4976 - 4977
[8] REGIOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO 1-ACYLPYRIDINIUM SALTS - A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-ALKYL(ARYL)PYRIDINES
COMINS, DL
ABDULLAH, AH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (22) : 4315 - 4319
[9] COMINS DL, 1986, TETRAHEDRON LETT, V27, P4549
[10] ENANTIOPURE 2,3-DIHYDRO-4-PYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC SYNTHESES OF THE QUINOLIZIDINE ALKALOIDS (+)-MYRTINE, (-)-LASUBINE-I, AND (+)-SUBCOSINE-I
COMINS, DL
LAMUNYON, DH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5807 - 5809

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