ON THE STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS - NUCLEOPHILE DEPENDENCE

被引：55
作者：
DENMARK, SE
ALMSTEAD, NG
机构：
[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 23期
关键词：
D O I：
10.1021/jo00023a002
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The stereoselective allylation of chiral dioxane acetals 1 was found to be highly dependent on the nature of allymetal reagent in the following order: Ph3Si (19/1) < Me3Si (58/1) < Ph3Sn (90/1) < Me3Ge (100/1) < n-Bu3Sn (> 300/1). The allylation with allytributylstannane was significantly more selective than allytrimethylsilane for a number of chiral dioxane acetals examined.
引用
收藏
页码：6485 / 6487
页数：3
相关论文
共 8 条
[1]   CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].
ALEXAKIS, A ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511
[2]  
DENMARK SE, IN PRESS J AM CHEM S
[3]   KINETICS OF THE REACTIONS OF ALLYLSILANES, ALLYLGERMANES, AND ALLYLSTANNANES WITH CARBENIUM IONS [J].
HAGEN, G ;
MAYR, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :4954-4961
[4]  
JOHNSON WS, 1984, TETRAHEDRON LETT, V25, P3951, DOI 10.1016/0040-4039(84)80038-6
[5]  
MUKAIYAMA T, 1987, SYNTHESIS-STUTTGART, P1043
[6]   MECHANISTIC INSIGHT INTO ALLYLMETAL-THIOACETAL REACTIONS EMPLOYING 2-ACETOXY-2-PHENYLACETALDEHYDE THIOACETALS [J].
SATO, T ;
OTERA, J ;
NOZAKI, H .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6116-6121
[7]  
Seebach D., 1986, MODERN SYNTHETIC MET, V4, P125
[8]   IMPORTANCE OF THE TIMING OF BOND BREAKING AND BOND MAKING IN ACETAL TEMPLATES - ENANTIODIVERGENT SYNTHESIS OF STEROIDAL SIDE-CHAINS [J].
YAMAMOTO, Y ;
NISHII, S ;
YAMADA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7116-7117
1