Enantio- and diastereoselective synthesis of highly substituted benzazepines by a multicomponent strategy coupled with organocatalytic and enzymatic procedures.
J Org Chem
; 79(1): 339-51, 2014 Jan 03.
Article
en En
| MEDLINE
| ID: mdl-24328226
ABSTRACT
Enantiomerically pure 4,5-dihydro-1H-benzo[c]azepines with three contiguous stereogenic centers have been assembled by convergent strategy with a good control of diastereoselectivity. The two steps are as follows an asymmetric organocatalytic Mannich reaction performed on Boc-imines of o-(azidomethyl)benzaldehydes, followed by a one-pot Staudinger/aza-Wittig/Ugi-Joullié sequence. The latter reaction represents one of the first examples of diastereoselective Ugi three-component reaction on a seven-membered cyclic imine. The o-azidomethylbenzaldehydes have been synthesized employing a simple and efficient chemoenzymatic strategy from commercially available building blocks.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Benzaldehídos
/
Benzazepinas
Idioma:
En
Revista:
J Org Chem
Año:
2014
Tipo del documento:
Article
País de afiliación:
Italia