Literature DB >> 19199765

NHC-catalyzed ring expansion of oxacycloalkane-2-carboxaldehydes: a versatile synthesis of lactones.

Li Wang1, Karen Thai, Michel Gravel.   

Abstract

Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.

Entities:  

Year:  2009        PMID： 19199765     DOI： 10.1021/ol8029005

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

2.  Regio- and Stereospecific 1,3-Allyl Group Transfer Triggered by a Copper-Catalyzed Borylation/ortho-Cyanation Cascade.

Authors:  Yang Yang
Journal:  Angew Chem Int Ed Engl       Date:  2015-10-28       Impact factor: 15.336

3.  A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization.

Authors:  Xingkuan Chen; Hongling Wang; Kazuki Doitomi; Chong Yih Ooi; Pengcheng Zheng; Wangsheng Liu; Hao Guo; Song Yang; Bao-An Song; Hajime Hirao; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2017-05-25       Impact factor: 14.919
  3 in total

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