6533b858fe1ef96bd12b6549
RESEARCH PRODUCT
Catalytic enantioselective aza-Reformatsky reaction with seven-membered cyclic imines dibenzo[b,f][1,4]oxazepines
Lode De MunckVerena SukowskiJosé R. PedroCarlos VilaM. Carmen Muñozsubject
010405 organic chemistryStereochemistryOrganic ChemistryEthyl iodoacetateChiral ligandEnantioselective synthesis010402 general chemistry01 natural sciences0104 chemical sciencesCatalysisProlinolReaccions químiqueschemistry.chemical_compoundchemistryYield (chemistry)Reformatsky reactionEnantiomeric excessQuímica orgànicadescription
A catalytic enantioselective aza-Reformatsky reaction is reported with cyclic dibenzo[b,f][1,4]oxazepines and ethyl iodoacetate leading to the synthesis of chiral ethyl 2-(10,11-dihydrodibenzo[b,f][1,4]oxazepin-11-yl)acetate derivatives with excellent yields and high enantioselectivities (up to 98% yield and 97 : 3 er) using a readily available diaryl prolinol L4 as the chiral ligand and Me2Zn as the zinc source under an air atmosphere. Furthermore, different transformations were carried out with the corresponding chiral β-amino esters, preserving in all cases the optical purity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-01-01 |