Lewis acid catalyzed cycloaddition of methylenecyclopropanes with salicylaldehydes.
Lewis acid catalyzed cycloaddition of methylenecyclopropanes (MCPs) with o-quinonemethide analogues, derived from the corresponding salicylaldehydes and CH(OEt)(3), produces the corresponding cycloadducts 3 in moderate to high yields at room temperature (20 degrees C). Moreover, the compounds 3 can be transformed to the indene derivatives 5 at high temperature. Plausible mechanisms have been proposed on the basis of control experiments.
Jiang
Min
M
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
Shi
Min
M
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D013696:Temperature
D000447:Aldehydes; D003521:Cyclopropanes; C508672:methylenecyclopropane; C013243:salicylaldehyde; D006046:Gold