A convenient method for the preparation of unsymmetrical bis-aldols by way of sequential two aldol reactions

Hidehiro Arai, Isamu Shiina, Teruaki Mukaiyama

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Unsymmetrical alkyl 2-hydroxy-1-(1-hydroxyalkyl)alkyl ketones (bis-aldols) are successfully synthesized by way of sequential two aldol reactions using α-bromo ketones and two different aldehydes. In the first reaction, α-bromo-β-stannyloxy ketones are formed by tin(II) trifluoromethanesulfornate-promoted aldol reaction of α-bromo ketones with several aldehydes. Bis-aldols are then formed via the second aldol reaction between another aldehydes and dianionic enolates generated by the reduction of α-bromo-β-metalloxy ketones with titanium(IV) iodide and copper.

Original languageEnglish
Pages (from-to)118-119
Number of pages2
JournalChemistry Letters
Issue number2
Publication statusPublished - 1 Jan 2001

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