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

页码：6485 / 6487

页数：3

共 8 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS
ALEXAKIS, A
MANGENEY, P
[J]. 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
HAGEN, G
MAYR, H
[J]. 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
SATO, T
OTERA, J
NOZAKI, H
[J]. 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
YAMAMOTO, Y
NISHII, S
YAMADA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7116 - 7117

← 1 →