Studies in Spiroketal Synthesis 1. Nucleophilic Addition to an Oxy-Stabilized Carbonium Ion Generated on a 1,7-Dioxaspiro[5.5]undecane Ring System

Keith T. Mead; Ronald Zemribo

doi:10.1055/s-1996-5687

Synlett 1996; 1996(11): 1063-1064
DOI: 10.1055/s-1996-5687

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Studies in Spiroketal Synthesis 1. Nucleophilic Addition to an Oxy-Stabilized Carbonium Ion Generated on a 1,7-Dioxaspiro[5.5]undecane Ring System

Keith T. Mead^* , Ronald Zemribo

^*Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA, Fax +1 (601) 3251618, e-mail kmead@ra.msstate.edu

Abstract

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The low temperature reaction of 2-methoxy spiroketal 5 with a series of silane nucleophiles has been studied. The reaction was found to be Lewis acid - dependent, and sensitive to changes in both solvent and silane reagent. When the nucleophile is carbon - based, the product of C(2)-substitution is diastereomerically pure.

spiroketals - oxocarbenium ions - silane nucleophiles - nucleophilic addition

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