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Asymmetric Phase‐Transfer‐Catalyzed Intramolecular N‐Alkylation of Indoles and Pyrroles: A Combined Experimental and Theoretical Investigation
Author(s) -
Bandini Marco,
Bottoni Andrea,
Eichholzer Astrid,
Miscione Gian Pietro,
Stenta Marco
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000560
Subject(s) - intramolecular force , enantioselective synthesis , catalysis , alkylation , chemistry , combinatorial chemistry , substrate (aquarium) , computational chemistry , phase (matter) , organic chemistry , oceanography , geology
Asymmetric phase‐transfer catalysis (PTC) has risen to prominence over the last decade as a straightforward synthetic methodology for the preparation of pharmacologically active compounds in enantiomerically pure form. However, the complex interplay of weak nonbonded interactions (between catalyst and substrate) that could account for the stereoselection in these processes is still unclear, with tentative pictorial mechanistic representations usually proposed. Here we present a full account dealing with the enantioselective phase‐transfer‐catalyzed intramolecular aza‐Michael reaction (IMAMR) of indolyl esters, as a valuable synthetic tool to obtain added‐value compounds, such as dihydro‐pyrazinoindolinones. A combined computational and experimental investigation has been carried out to elucidate the key mechanistic aspects of this process.