Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation

Barbara A. Messerle*, Khuong Q. Vuong

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The indium complex [Ir(PyP)(CO) 2]BPh 4 where PyP = 1-[2-(diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereo selective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-ethynylhexane-1,6-diol. The cycloadditions occur in all but one case with quantitative conversion in under 24 h at 120 °C.

Original languageEnglish
Pages (from-to)385-390
Number of pages6
JournalPure and Applied Chemistry
Volume78
Issue number2
DOIs
Publication statusPublished - Feb 2006
Externally publishedYes

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