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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 11
BKCSDE 29(11)
November 20, 2008 

 
Title
Regioselective Synthesis of Poly-Substituted Pyrroles from Baylis-Hillman
Adducts via the [3+1+N] Annulation Strategy
Author
Jeong Mi Kim, Sangku Lee, Se Hee Kim, Hyun Seung Lee, Jae Nyoung Kim*
Keywords
Pyrroles, Baylis-Hillman adducts, Barbier reaction, PCC, Aerobic oxidation
Abstract
Poly-substituted pyrrole derivatives were synthesized from Baylis-Hillman adducts via the following consecutive reactions comprised of (i) bromination of the Baylis-Hillman adduct, (ii) In-mediated Barbier reaction with aldehyde, (iii) PCC oxidation to α-methylene-γ-keto ester, (iv) reaction with amine to form enamine intermediate, (v) Michael type cyclization, and the final (vi) aerobic oxidation.
Page
2215 - 0
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