Ir-catalyzed allylic amination/ring-closing metathesis: a new route to enantioselective synthesis of cyclic beta-amino alcohol derivatives.
Ir-catalyzed allylic aminations of (E)-4-benzyloxy-2-butenyl methyl carbonate with benzylamine using Feringa's (Sa,Sc,Sc)-phosphoramidite as a chiral ligand afforded linear-aminated achiral product N,O-dibenzyl-4-amino-2-buten-1-ol regioselectively (linear/branched = >99/1), whereas the (E)-5-benzyloxy-2-pentenyl methyl carbonate showed completely opposite regioselectivity (linear/branched = >1/99) and afforded the optically active (3R)-N,O-dibenzylated 3-amino-1-penten-5-ol with very high enantioselectivity (96% ee), which was used as a key intermediate for the effective synthesis of various cyclic beta-amino alcohol derivatives through ring-closing metathesis in high yields.
Lee
Jun Hee
JH
Division of Nano Science (BK21)/Department of Chemistry, Ewha Womans University, 11-1 Daehyun-Dong, Seodaemun-Gu, 120-750 Seoul, Korea.
Shin
Seunghoon
S
Kang
Jahyo
J
Lee
Sang-gi
SG
D000498:Allyl Compounds / Q000737:chemistry*; D000586:Amination; D000605:Amino Alcohols / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D007495:Iridium / Q000737:chemistry; D013237:Stereoisomerism
D000498:Allyl Compounds; D000605:Amino Alcohols; D007495:Iridium