Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels-Alder reaction of ß,γ-unsaturated α-keto esters.
Org Biomol Chem
; 13(21): 5875-9, 2015 Jun 07.
Article
in En
| MEDLINE
| ID: mdl-25920697
ABSTRACT
We describe the stereoselective synthesis of polyring-fused heterocyclic compounds based on diene-transmissive hetero-Diels-Alder reactions utilizing ß,γ-unsaturated α-keto esters. This protocol involves the initial endo- or exo-selective Diels-Alder (DA) reactions with electron-rich dienophiles, methylenation of the ester carbonyl groups with the Tebbe reagent, and a stereoselective second DA reaction with electron-deficient dienophiles. The use of enantioselective DA reactions in the initial reaction enables access to chiral polyring-fused heterocyclic compounds with multiple chiral centres.
Full text:
1
Database:
MEDLINE
Main subject:
Polyenes
/
Cycloaddition Reaction
/
Heterocyclic Compounds
Language:
En
Year:
2015
Type:
Article