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Formal carbene insertion into CO double bond: A facile approach to the synthesis of 2H-chromenes
Authors:Mingfeng Li  Rui Chu  Yun Zhao  Wenhao Hu  Shunying Liu
Institution:Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Rd., Shanghai, 200062, China
Abstract:A formal carbene insertion into C/>O double bonds of 2-hydroxycinnamaldehydes catalyzed by Rh<sub>2</sub>(esp)<sub>2</sub> with Na<sub>2</sub>CO<sub>3</sub> as additive has been disclosed by using aryldiazoacetates as carbene precursors. 2<em>H</em>-chromenes with a quaternary carbon at C-2 position were readily obtained from simple starting materials in good yields with excellent diastereoselectivity under mild reaction conditions in one pot. The reaction mechanism was investigated and proposed as the formation of epoxide intermediate from Rh(II)-associated carbene and (<em>E</em>)-2-hydroxycinnamaldehyde and followed by a cascade epoxide ring-opening procedure in which the (<em>E</em>)-intermediate was converted into the (<em>Z</em>)-intermediate to give (<em>Z</em>)-products.</td> </tr> <tr> <td align=
Keywords:Carbene insertion reaction  Aryldiazoacetates  Quaternary carbon formation  Chromenes  Transition metal catalysis
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