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Enantioselective Syntheses of Corynanthe Alkaloids by Chiral Brønsted Acid and Palladium Catalysis
Author(s) -
Wanner Martin J.,
Claveau Elise,
van Maarseveen Jan H.,
Hiemstra Henk
Publication year - 2011
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.201103150
Subject(s) - enantioselective synthesis , tsuji–trost reaction , chemistry , phosphoric acid , intramolecular force , catalysis , palladium , nucleophile , indole test , organic chemistry , alkylation , combinatorial chemistry
Synergistic catalysis : Three indole alkaloids (−)‐corynantheidine, (+)‐corynantheine and (+)‐dihydro‐corynantheine were prepared following a short and common strategy based on the binol phosphoric acid catalyzed enantioselective Pictet–Spengler reaction, followed by closure of the final ring by an intramolecular Tsuji–Trost‐type Pd‐catalyzed allylic alkylation by using an α‐ketoester‐derived enolate as the nucleophile (see scheme).