Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.
J Am Chem Soc
; 135(23): 8504-7, 2013 Jun 12.
Article
in En
| MEDLINE
| ID: mdl-23713683
ABSTRACT
An asymmetric intermolecular reaction between enals and nitroalkenes to yield δ-nitroesters has been developed, catalyzed by a novel chiral N-heterocyclic carbene. Key to this work was the development of a catalyst that favors the δ-nitroester pathway over the established Stetter pathway. The reaction proceeds in high stereoselectivity and affords the previously unreported syn diastereomer. We also report an operationally facile two-step, one-pot procedure for the synthesis of δ-lactams.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Alkenes
/
Heterocyclic Compounds
/
Lactams
/
Methane
/
Nitro Compounds
Language:
En
Journal:
J Am Chem Soc
Year:
2013
Document type:
Article
Affiliation country:
United States