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Communication | Special issue | Vol 67, No. 1, 2006, pp.119-122
Published online, 30th August, 2005
DOI: 10.3987/COM-05-S(T)35
Enantioselective Alkylation of Reissert Compounds in Phase Transfer Catalysed Reactions

Danuta Brózda, Krzysztof Hoffman, and Maria D. Rozwadowska*

*Department of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznán, Poland


Isoquinoline Reissert compounds were alkylated under phase-transfer reaction conditions using chiral quaternary ammonium salts derived from Cinchona alkaloids as catalysts. The best stereoselectivity (ee up to 65%) was achieved in the alkylation of 1-cyano-2-phenoxycarbonyl-1.2-dihydroisoquinoline (1d), catalysed by N-benzylcynchoninium bromide (3a), carried in toluene/50% NaOH biphasic system.