Utilization of aldoses as a carbonyl source in cyclocarbonylation of enynes.
The reaction of enynes with acetyl-masked aldoses in the presence of a rhodium(I) catalyst resulted in cyclocarbonylation, thus avoiding the direct use of carbon monoxide, to afford bicyclic cyclopentenones. In rhodium catalysis, aldoses serve as a carbon monoxide equivalent by donating their carbonyl moieties on the acyclic aldehyde form to enynes. A variety of aldoses, including D-glucose, D-mannose, D-galactose, D-xylose, and D-ribose, can be used as a carbonyl source. Using the method, a wide variety of enynes were cyclocarbonylated in 22-67% yields. An asymmetric variant also proceeded with moderate to high enantioselectivity.
Ikeda
Keiichi
K
Graduate School of Materials Science, Nara Institute of Science and Technology, Takayama, Ikoma, Nara 630-0192, Japan.
Morimoto
Tsumoru
T
Kakiuchi
Kiyomi
K
D000480:Alkynes / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D002241:Carbohydrates; D007659:Ketones; D009942:Organometallic Compounds; D012238:Rhodium