An asymmetric synthesis of (2S,5S)-5-substituted azepane-2-carboxylate derivatives.
J Org Chem
; 76(6): 1937-40, 2011 Mar 18.
Article
em En
| MEDLINE
| ID: mdl-21275376
ABSTRACT
To facilitate a drug discovery project, we needed to develop a robust asymmetric synthesis of (2S,5S)-5-substituted-azepane-2-carboxylate derivatives. Two key requirements for the synthesis were flexibility for elaboration at C5 and suitability for large scale preparation. To this end we have successfully developed a scalable asymmetric synthesis of these derivatives that starts with known hydroxy-ketone 8. The key step features an oxidative cleavage of aza-bicyclo[3.2.2]nonene 14, which simultaneously generates the C2 and C5 substituents in a stereoselective manner.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ácidos Carboxílicos
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article