On the Stereoselective Opening of Chiral Dioxane Acetals. Nucleophile Dependence

Scott E. Denmark; Neil G. Almstead

doi:10.1021/jo00023a002

On the Stereoselective Opening of Chiral Dioxane Acetals. Nucleophile Dependence

Scott E. Denmark, Neil G. Almstead

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The stereoselective allylation of chiral dioxane acetals 1 was found to be highly dependent on the nature of allylmetal reagent in the following order: Ph₃Si (19/1) < Me₃Si (58/1) < Ph₃Sn (90/1) < Me₃Ge (100/1) < n-Bu₃Sn (>300/1). The allylation with allyltributylstannane was significantly more selective than allyltrimethylsilane for a number of chiral dioxane acetals examined.

Original language	English (US)
Pages (from-to)	6485-6487
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	56
Issue number	23
DOIs	https://doi.org/10.1021/jo00023a002
State	Published - Nov 1 1991

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00023a002

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abstract = "The stereoselective allylation of chiral dioxane acetals 1 was found to be highly dependent on the nature of allylmetal reagent in the following order: Ph3Si (19/1) < Me3Si (58/1) < Ph3Sn (90/1) < Me3Ge (100/1) < n-Bu3Sn (>300/1). The allylation with allyltributylstannane was significantly more selective than allyltrimethylsilane for a number of chiral dioxane acetals examined.",

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year = "1991",

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N2 - The stereoselective allylation of chiral dioxane acetals 1 was found to be highly dependent on the nature of allylmetal reagent in the following order: Ph3Si (19/1) < Me3Si (58/1) < Ph3Sn (90/1) < Me3Ge (100/1) < n-Bu3Sn (>300/1). The allylation with allyltributylstannane was significantly more selective than allyltrimethylsilane for a number of chiral dioxane acetals examined.

AB - The stereoselective allylation of chiral dioxane acetals 1 was found to be highly dependent on the nature of allylmetal reagent in the following order: Ph3Si (19/1) < Me3Si (58/1) < Ph3Sn (90/1) < Me3Ge (100/1) < n-Bu3Sn (>300/1). The allylation with allyltributylstannane was significantly more selective than allyltrimethylsilane for a number of chiral dioxane acetals examined.

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On the Stereoselective Opening of Chiral Dioxane Acetals. Nucleophile Dependence

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