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Guanidine-Catalyzed γ-Selective Morita-Baylis-Hillman Reactions on α,γ-Dialkyl-Allenoates: Access to Densely Substituted Heterocycles

Philipp Selig*, Aleksej Turočkin, William Raven

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Landoltweg 1, 52074 Aachen, Germany, Email: philipp.seligrwth-aachen.de

P. Selig, A. Turočkin, W. Raven, Synlett, 2013, 24, 2535-2539.

DOI: 10.1055/s-0033-1339471 (free Supporting Information)


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Abstract

N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) catalyzes a Morita-Baylis-Hillman reaction of previously hard-to-activate α,γ-dialkyl allenoate substrates. The obtained densely substituted allenic alcohols could be further converted into 2,5-dihydrofuran and 2H-pyran-2-one heterocyclic structures with challenging substitution patterns.

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Key Words

Baylis-Hillman reaction, allenes, catalysis, nucleophiles, guanidines, cyclization


ID: J60-Y2013