N-silyl-tethered radical cyclizations: a new synthesis of gamma-amino alcohols.
[reaction: see text] Various allylic and propargylic amines bearing a protecting group (PG) have been employed in N-silyl-tethered radical cyclizations. The resulting silapyrrolidine adducts could be smoothly oxidized, creating access to gamma-amino alcohols. The silylation, radical cyclization, and oxidation reactions could be consolidated in a one-pot process.
Blaszykowski
Christophe
C
Laboratoire de Chimie Organique, UMR CNRS 7611, Université Pierre et Marie Curie, Case 229, 4 place Jussieu, 75252 Paris Cedex 05, France.
Dhimane
Anne-Lise
AL
Fensterbank
Louis
L
Malacria
Max
M
D000499:Allylamine / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis*; D003500:Cyclization; D017646:Organosilicon Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry
D000605:Amino Alcohols; D017646:Organosilicon Compounds; D011759:Pyrrolidines; D000499:Allylamine