Rhodium-Catalyzed Decarbonylation of Aldoses

Rune Monrad, Robert Madsen

Research output: Contribution to journalJournal articlepeer-review

Abstract

A catalytic procedure is described for decarbonylation of unprotected aldoses to afford alditols with one less carbon atom. The reaction is performed with the rhodium complex Rh(dppp)2Cl in a refluxing diglyme - DMA solution. A slightly improved catalyst turnover is observed when a catalytic amount of pyridine is added. Under these conditions most hexoses and pentoses undergo decarbonylation into the corresponding pentitols and tetrols in isolated yields around 70%. The reaction has been applied as the key transformation in a five-step synthesis of L-threose from D-glucose.
Original languageEnglish
JournalThe Journal of Organic Chemistry
Volume72
Issue number25
Pages (from-to)9782-9785
ISSN0022-3263
DOIs
Publication statusPublished - 2007

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