Construction of complex bisether-bridged medium-sized cyclic compounds from o-(1-(acyloxy)propargyl)benzaldehydes under base and acid catalysis
We report herein our serendipitous discovery of the rapid and straightforward accesses to unprecedented diverse complex molecular structures from readily available starting materials. Catalyzed by 1,8-diazabicyclo[5.4.0]undec-7-ene under mild conditions, o-(1-(acyloxy)propargyl)benzaldehydes 1 underwent efficient and selective dimerization reactions to produce novel complex bisether-bridged tricyclic products 3 and 4. The reactions proceeded most probably through dimerizations between 3-methylene-3H-isochromene intermediate and its zwitterionic resonance structures which were generated from a concerted 6-πelectrocyclic ring closure reaction from the initially formed (2-formylphenyl)allene intermediates derived directly from o-(1-(acyloxy)propargyl)benzaldehydes. Treatment of the resulting product simply with NaOEt in ethanol and aqueous HCl, respectively, enabled further development of complex molecular diversities.
Zhao, Yun-Long,Cheng, Ying
p. 11114 - 11124
(2019/09/30)
Stereoselective synthesis of nipecotic acid derivatives via palladium-catalyzed decarboxylative cyclization of γ-methylidene-δ- valerolactones with imines
(Chemical Equation Presented) A new synthetic method of multisubstituted nipecotic acid (piperidine-3-carboxylic acid) derivatives has been developed by way of palladium-catalyzed decarboxylative cyclization of γ-methylidene- δ-valerolactones with (mines.
Shintani, Ryo,Murakami, Masataka,Hayashi, Tamio
supporting information; experimental part
p. 457 - 459
(2009/07/11)
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