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 language | English |
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Journal | The Journal of Organic Chemistry |
Volume | 72 |
Issue number | 25 |
Pages (from-to) | 9782-9785 |
ISSN | 0022-3263 |
DOIs | |
Publication status | Published - 2007 |