Sonogashira Couplings of Halo‐ and Epoxy‐Halo‐ exo ‐Glycals: Concise Entry to Carbohydrate‐Derived Enynes | Zendy

Gómez Ana M. | Zendy; Barrio Aitor | Zendy; Pedregosa Ana | Zendy; Uriel Clara | Zendy; Valverde Serafín | Zendy; López J. Cristóbal | Zendy

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Sonogashira Couplings of Halo‐ and Epoxy‐Halo‐ exo ‐Glycals: Concise Entry to Carbohydrate‐Derived Enynes

Author(s) -

Gómez Ana M.,

Barrio Aitor,

Pedregosa Ana,

Uriel Clara,

Valverde Serafín,

López J. Cristóbal

Publication year - 2010

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201000170

Subject(s) - sonogashira coupling , chemistry , furanose , glycal , pyranose , stereoselectivity , stereochemistry , mannose , catalysis , combinatorial chemistry , organic chemistry , palladium , ring (chemistry)

Furanose‐ and pyranose‐derived mono‐ and dihalo‐ exo ‐glycals undergo Sonogashira coupling reactions in the presence of Pd catalysts to give carbohydrate‐derived enynes in a completely stereoselective manner. On the other hand, a furanose‐derived 2,3‐anhydrohalo‐ exo ‐glycal, available from D ‐mannose in five steps, undergoes Pd 0 ‐catalyzed Sonogashira coupling, leading to 2‐deoxyenynes.

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