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Palladium‐Catalyzed Decarboxylative Cycloaddition of Vinylethylene Carbonates with Formaldehyde: Enantioselective Construction of Tertiary Vinylglycols
Author(s) -
Khan Ajmal,
Zheng Renfeng,
Kan Yuhe,
Ye Jiang,
Xing Juxiang,
Zhang Yong Jian
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403754
Subject(s) - palladium , phosphoramidite , enantioselective synthesis , catalysis , cycloaddition , chemistry , acetal , ligand (biochemistry) , formaldehyde , organic chemistry , methylene , receptor , dna , biochemistry , oligonucleotide
An efficient method for the enantioselective construction of tertiary vinylglycols through a palladium‐catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with formaldehyde was developed. By using a palladium complex generated in situ from [Pd 2 (dba) 3 ]⋅CHCl 3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process allows conversion of racemic 4‐substituted 4‐vinyl‐1,3‐dioxolan‐2‐ones into the corresponding 1,3‐dioxolanes, as methylene acetal protected tertiary vinylglycols, in high yields with good to excellent enantioselectivities.