Access to oxoquinoline heterocycles by N-heterocyclic carbene catalyzed ester activation for selective reaction with an enone.
Organocatalytic ester activation is developed for a highly selective cascade reaction between saturated esters and amino enones. The reaction involves activation of the β-carbon atom of the ester as a key step. This method allows a single-step access to multicyclic oxoquinoline-type heterocycles with high enantiomeric ratios.
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
Zhenqian
Z
Fu
Ke
K
Jiang
Tingshun
T
Zhu
Jaume
J
Torres
Yonggui Robin
YR
Chi
D000475:Alkenes / Q000737:chemistry*; D002243:Carbolines / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry*
D000475:Alkenes; D002243:Carbolines; D004952:Esters; D006571:Heterocyclic Compounds; D007659:Ketones; D015363:Quinolones; C100106:dicarbine
CH activation; N-heterocyclic carbene; cyclization; heterocycles; organocatalysis