THE STEREOCONTROLLED FORMATION OF CYCLIC VICINAL CIS-DIOLS VIA A SAMARIUM DIIODIDE PINACOL COUPLING OF DIALDEHYDES

被引:113
作者
CHIARA, JL [1 ]
CABRI, W [1 ]
HANESSIAN, S [1 ]
机构
[1] UNIV MONTREAL,DEPT CHEM,CP 6128,SUCC A,MONTREAL H3C 3J7,QUEBEC,CANADA
关键词
D O I
10.1016/S0040-4039(00)92024-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aliphatic 1,5- and 1,6 dialdehydes with and without alpha-substituents, as well as derivatives of carbohydrate dialdehydes undergo a pinacol coupling reaction in the presence of SmI2 to give cis-diols as the preponderant products. When alpha-alkoxy groups are present, the diol has an orientation that is opposite to such groups.
引用
收藏
页码:1125 / 1128
页数:4
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