STEREOCHEMICAL STUDIES ON THE ADDITION OF ALLYLSTANNANES TO ALDEHYDES - THE S-E' COMPONENT

被引:43
作者
DENMARK, SE
HOSOI, S
机构
[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
关键词
D O I
10.1021/jo00097a009
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The disposition of the tin electrofuge in the cyclization of (l)-1 and (u)-1 has been established to be anti S-E' under Lewis and Bronsted acid promotion and syn S-E' under thermal conditions.
引用
收藏
页码:5133 / 5135
页数:3
相关论文
共 34 条
[1]   SYNTHESIS OF ALLYSTANNANES AND VINYLSTANNANES BY THE STANNYL-CUPRATION OF ALLENES [J].
BARBERO, A ;
CUADRADO, P ;
FLEMING, I ;
GONZALEZ, AM ;
PULIDO, FJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :327-331
[2]   CATALYTIC ASYMMETRIC-SYNTHESIS OF HOMOALLYLIC ALCOHOLS [J].
COSTA, AL ;
PIAZZA, MG ;
TAGLIAVINI, E ;
TROMBINI, C ;
UMANIRONCHI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7001-7002
[3]   REACTIVITY OF TETRAALLYLTIN AND ALLYLTRIALKYLTIN WITH ALDEHYDES, KETONES AND EPOXIDES [J].
DAUDE, G ;
PEREYRE, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 190 (01) :43-52
[4]   SNCL4(4-TERT-BUC6H4CHO)2 - X-RAY CRYSTAL-STRUCTURE, SOLUTION NMR, AND IMPLICATIONS FOR REACTIONS AT COMPLEXED CARBONYLS [J].
DENMARK, SE ;
HENKE, BR ;
WEBER, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (08) :2512-2514
[5]   STEREOCHEMICAL STUDIES ON THE ADDITION OF ALLYLSILANES TO ALDEHYDES - THE S-E' COMPONENT [J].
DENMARK, SE ;
ALMSTEAD, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5130-5132
[6]   STEREOCHEMISTRY OF ALLYLMETAL ALDEHYDE CONDENSATIONS .2. ALLYLSTANNANES [J].
DENMARK, SE ;
WEBER, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (25) :7970-7971
[7]   STEREOCHEMICAL AND SPECTROSCOPIC STUDIES ON THE REACTION OF ALLYLSTANNANES WITH ALDEHYDES [J].
DENMARK, SE ;
WEBER, EJ ;
WILSON, TM ;
WILLSON, TM .
TETRAHEDRON, 1989, 45 (04) :1053-1065
[8]  
Fleming I., 1991, COMPREHENSIVE ORGANI, P563
[9]  
Fleming I., 1989, ORG REACTIONS, V37, P57
[10]   CYCLIC TRANSITION-STATE IN THE ACID-CATALYZED INTRAMOLECULAR ALLYLSTANNANE-ALDEHYDE CONDENSATION [J].
GEVORGYAN, V ;
KADOTA, I ;
YAMAMOTO, Y .
TETRAHEDRON LETTERS, 1993, 34 (08) :1313-1316