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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.