An unprecedented stereoselective [2+2] cycloreversion of cyclobutanones.
A one-pot metathetic ring opening of substituted bicyclo[3.2.0]heptenones to linear polyene ketones is described. The reaction proceeds with conservation of the endocyclic (Z)-double bond. Exo-substituted vinylcyclobutanones result in (4Z,6E)-configured trienones, while endo-substituted phenyl derivatives generate (4Z,6Z)-configured dienones.
Ji
Xiufang
X
Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
Wang
Quanrui
Q
Goeke
Andreas
A
D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003503:Cyclobutanes; D007659:Ketones