Synthesis of α-Methylene-β-Pyrrole Esters via Organocatalytic Regioselective Allylic Substitutions of Morita-Baylis-Hillman Acetates

• Published in: Bulletin of the Korean Chemical Society Vol. 29; no. 9; pp. 1835 - 1838
• Main Authors: 조창우, Su-Hyun Kwon
• Format: Journal Article
• Language: English
• Published: 대한화학회 20.09.2008
• Subjects: 화학
• ISSN: 0253-2964; 1229-5949
• DOI: 10.5012/bkcs.2008.29.9.1835

Recently, stoichiometric and organocatalytic variants of allylic substitutions of Morita-Baylis-Hillman (MBH) acetates via an SN2'-SN2' tandem mechanism have come to light. Different types of nucleophiles such as TsNH₂, phthalimides (N-based nucleophiles), dialkyl malonates, 2-silyloxyfuran (C-based nucleophiles), and phenols (O-based nucleophiles) have been reported in the organocatalytic allylic substitutions of MBH acetates. However, to the best of our knowledge, there are no examples stating the use of pyrroles as N-based heterocyclic nucleophiles in the organocatalytic allylic substitutions of MBH acetates, even though pyrroles are important moieties in many natural products, pharmaceuticals, and materials. Here, the first examples of organocatalytic allylic substitutions using pyrroles as N-based heterocyclic nucleophiles for the synthesis of various α-methylene-β-pyrroles esters will be discussed. KCI Citation Count: 8