ENANTIOSELECTIVE RADICAL-MEDIATED REDUCTION OF ALPHA-IODOLACTONE USING TRIBUTYLTIN HYDRIDE IN THE PRESENCE OF A CHIRAL AMINE AND A LEWIS-ACID

被引：63

作者：

MURAKATA, M ^{[1
]}

TSUTSUI, H ^{[1
]}

HOSHINO, O ^{[1
]}

机构：

[1] SCI UNIV TOKYO,FAC PHARMACEUT SCI,SHINJUKU KU,TOKYO 162,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 04期

关键词：

D O I：

10.1039/c39950000481

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective radical-mediated reduction of alpha-methoxymethyl-alpha-iododihydrocoumarin 1 using tributyltin hydride is realized in up to 62% enantiomeric excess (e,e.) (88% chemical yield) by combination of chiral diamine 2 and magnesium iodide.

引用

收藏

页码：481 / 482

页数：2

相关论文

共 15 条

[1] 1,2-ASYMMETRIC INDUCTION IN RADICAL REACTIONS - DEUTERATION AND ALLYLATION REACTIONS OF BETA-OXY-ALPHA-BROMO ESTERS [J].

CURRAN, DP ;

RAMAMOORTHY, PS .

TETRAHEDRON, 1993, 49 (22) :4841-4858

[2] ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS WITH DIARYLUREAS [J].

CURRAN, DP ;

KUO, LH .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3259-3261

[3] THE STEREOSELECTIVITY OF INTERMOLECULAR FREE-RADICAL REACTIONS [J].

GIESE, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1989, 28 (08) :969-980

[4] STEREOSELECTIVE CHELATION-CONTROLLED REDUCTION OF ALPHA-IODO-BETA-ALKOXY ESTERS UNDER RADICAL CONDITIONS [J].

GUINDON, Y ;

LAVALLEE, JF ;

LLINASBRUNET, M ;

HORNER, G ;

RANCOURT, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9701-9702

[5] INVESTIGATION OF A MODEL FOR 1,2-ASYMMETRIC INDUCTION IN REACTIONS OF ALPHA-CARBALKOXY RADICALS - A STEREOCHEMICAL COMPARISON OF REACTIONS OF ALPHA-CARBALKOXY RADICALS AND ESTER ENOLATES [J].

HART, DJ ;

KRISHNAMURTHY, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) :4457-4470

[6] 1,2-ASYMMETRIC INDUCTION IN RADICAL-MEDIATED ALLYLATION OF DIETHYL (2S,3S)-3-BROMO-2-OXYSUCCINATES - EFFICIENT STEREOSELECTIVITY ENHANCEMENT BY COMPLEXATION WITH EU(FOD)(3) [J].

NAGANO, H ;

KUNO, Y .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (08) :987-988

[7] LEWIS ACID-PROMOTED DIASTEREOSELECTIVE RADICAL CYCLIZATION USING CHIRAL ALPHA,BETA-UNSATURATED ESTERS [J].

NISHIDA, M ;

UEYAMA, E ;

HAYASHI, H ;

OHTAKE, Y ;

YAMAURA, Y ;

YANAGINUMA, E ;

YONEMITSU, O ;

NISHIDA, A ;

KAWAHARA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) :6455-6456

[8] ACYCLIC STEREOCHEMICAL CONTROL IN FREE-RADICAL REACTIONS [J].

PORTER, NA ;

GIESE, B ;

CURRAN, DP .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :296-304

[9] REACTIONS OF SULFINYLATED RADICALS - SOLVENT EFFECT AND EFFICIENT STEREOSELECTIVITY ENHANCEMENT BY COMPLEXATION OF THE SULFINYL GROUP WITH LEWIS-ACIDS [J].

RENAUD, P ;

RIBEZZO, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7803-7805

[10] ALTERING THE STEREOCHEMISTRY OF ALLYLATION REACTIONS OF CYCLIC ALPHA-SULFINYL RADICALS - EFFECTS OF SOLVENTS AND LEWIS-ACIDS [J].

RENAUD, P ;

MOUFID, N ;

KUO, LH ;

CURRAN, DP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3547-3552