Diastereoselective [4 + 1] cycloaddition of alkenyl propargyl acetates with CO catalyzed by [RhCl(CO)2]2.
A class of alkenyl propargyl acetates, RCH(OAc)C≡CC(CH(3))═CH(2) (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents, up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.
Department of Chemistry, Sichuan University, Chengdu, China 610064.
Wei
W
Chen
Jia-Hui
JH
Tay
Xiao-Qi
XQ
Yu
Lin
L
Pu
D000085:Acetates / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010293:Pargyline / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D003517:Cyclopentanes; D009942:Organometallic Compounds; D002248:Carbon Monoxide; D010293:Pargyline; D012238:Rhodium; C013905:cyclopentenone