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Gold‐Catalyzed Stereocontrolled Synthesis of 2,3‐Bis(acetoxy)‐1,3‐dienes
Author(s) -
Huang Xiaogen,
de Haro Teresa,
Nevado Cristina
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900391
Subject(s) - phosphine , chemistry , alkene , ligand (biochemistry) , catalysis , stereochemistry , tandem , stereoselectivity , medicinal chemistry , organic chemistry , receptor , biochemistry , materials science , composite material
Change the ligand, change the stereochemistry : 2,3‐Bis(acetoxy)‐1,3‐dienes are obtained in a stereocontrolled manner by a novel tandem 1,2‐/1,2‐bis(acetoxy) rearrangement (see scheme, R 1 and R 2 are δ + stabilizing). Upon stabilization of the reaction intermediates, the ligand attached to gold controls the stereochemistry of the alkene in the second acetate migration, that is, N‐heterocyclic carbenes (NHC) favor cis alkenes, whereas phosphine ligands selectively afford trans olefins.