NHC-catalyzed reaction of enals with hydroxy chalcones: Diastereoselective synthesis of functionalized coumarins

Organic Letters

Volumn 15, Issue 7, 2013, Pages 1756-1759

  Bhunia, Anup ^a   Patra, Atanu ^a   Puranik, Vedavati G ^a   Biju, Akkattu T ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84875959949     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400562z     Document Type: Article

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40. Notably, the formation of functionalized coumarin 3 can also be rationalized by invoking the β-lactone intermediate E generated from cyclopentane intermediate C (Scheme 4) followed by the intramolecular opening of the β-lactone E to generate δ-lactone F and subsequent elimination of water. However, based on the apparent preference of δ-lactonization over β-lactonization as revealed by the competition experiments, this possibility can be ruled out at this point. For a related report, see: Kaeobamrung, J.; Bode, J. W. Org. Lett. 2009, 11, 677