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A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization.
Chen, Xingkuan; Wang, Hongling; Doitomi, Kazuki; Ooi, Chong Yih; Zheng, Pengcheng; Liu, Wangsheng; Guo, Hao; Yang, Song; Song, Bao-An; Hirao, Hajime; Chi, Yonggui Robin.
Afiliação
  • Chen X; Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Wang H; Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
  • Doitomi K; Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Ooi CY; Department of Biology and Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon Tong, Hong Kong 999078, China.
  • Zheng P; Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
  • Liu W; Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
  • Guo H; Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
  • Yang S; Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China.
  • Song BA; Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
  • Hirao H; Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
  • Chi YR; Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Nat Commun ; 8: 15598, 2017 05 25.
Article em En | MEDLINE | ID: mdl-28541276
The research in the field of asymmetric carbene organic catalysis has primarily focused on the activation of carbon atoms in non-aromatic scaffolds. Here we report a reaction mode of carbene catalysis that allows for aromatic aldehyde activation and remote oxygen atom functionalization. The addition of a carbene catalyst to the aldehyde moiety of 2-hydroxyl aryl aldehyde eventually enables dearomatization and remote OH activation. The catalytic process generates a type of carbene-derived intermediate with an oxygen atom as the reactive centre. Inexpensive achiral urea co-catalyst works cooperatively with the carbene catalyst, leading to consistent enhancement of the reaction enantioselectivity. Given the wide presence of aromatic moieties and heteroatoms in natural products and synthetic functional molecules, we expect our reaction mode to significantly expand the power of carbene catalysis in asymmetric chemical synthesis.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Nat Commun Assunto da revista: BIOLOGIA / CIENCIA Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Singapura País de publicação: Reino Unido

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Nat Commun Assunto da revista: BIOLOGIA / CIENCIA Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Singapura País de publicação: Reino Unido