Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.
We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate beta-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction.
Vora
Harit U
HU
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Moncecchi
Johannah R
JR
Epstein
Oleg
O
Rovis
Tomislav
T
D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis*; D001386:Azides / Q000138:chemical synthesis*; D002384:Catalysis; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000605:Amino Alcohols; D001386:Azides; D010080:Oxazoles; C030011:carbene; D008697:Methane