Rhodium-catalyzed formylation of organomercurials: application to efficient polyol synthesis.
The rhodium-catalyzed formylation of organomercurials-a new transformation of organomercurials-is reported. The addition of 0.50 equiv of 1,4-diazabicyclo[2.2.2]octane (DABCO) was found to promote the reaction, and it is postulated that the DABCO acts as a ligand for mercury. Several examples are presented to document the scope of the reaction. This reaction was developed in the context of a larger program focused on the development of efficient strategies for the synthesis of polyol-derived natural products, and an efficient (8 steps) synthesis of Tolypothrix pentaether that employs this methodology is reported.
Sarraf
S T
ST
Department of Chemistry, Columbia University, New York, New York 10027, USA.
Leighton
J L
JL
D000438:Alcohols / Q000138:chemical synthesis; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D000458:Cyanobacteria / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005561:Formates / Q000737:chemistry; D009941:Organomercury Compounds / Q000138:chemical synthesis*; D012238:Rhodium
D000438:Alcohols; D000475:Alkenes; D004987:Ethers; D005561:Formates; D009941:Organomercury Compounds; C415664:tolypothrix pentaether; C030544:formic acid; D012238:Rhodium