A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners.
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 beta- and gamma-lactams, can be employed.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Alonso
Jose M
JM
D000498:Allyl Compounds / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D006827:Hydantoins / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry; D010084:Oxidation-Reduction; D011720:Pyrazoles / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D000577:Amides; D006827:Hydantoins; D007094:Imides; D007769:Lactams; D023303:Oxazolidinones; D011720:Pyrazoles; D012428:Ruthenium