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A Practical Ruthenium‐Catalyzed Cleavage of the Allyl Protecting Group in Amides, Lactams, Imides, and Congeners
Author(s) -
Alcaide Benito,
Almendros Pedro,
Alonso Jose M.
Publication year - 2006
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.200501227
Subject(s) - enantiopure drug , ruthenium , amide , isomerization , allylic rearrangement , chemistry , catalysis , carbene , combinatorial chemistry , cleavage (geology) , stereochemistry , organic chemistry , enantioselective synthesis , materials science , fracture (geology) , composite material
A convenient methodology for the deprotection of N ‐allylic amide‐like moieties was developed. The first examples accounting for the ruthenium‐catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl 3 (oxidation step). A variety of substrates, including enantiopure multifunctional β‐ and γ‐lactams, can be employed.