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One‐Pot Three‐Component Syntheses of Indoloquinolizidine Derivatives Using an Organocatalytic Michael Addition and Subsequent Pictet–Spengler Cyclization
Author(s) -
Wu Xiaoyu,
Dai Xiaoyang,
Fang Huihui,
Nie Linlin,
Chen Jie,
Cao Weiguo,
Zhao Gang
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.201101468
Subject(s) - stereocenter , intramolecular force , michael reaction , conjugate , chemistry , indole test , pictet–spengler reaction , organocatalysis , cascade , component (thermodynamics) , stereochemistry , organic chemistry , catalysis , mathematics , enantioselective synthesis , chromatography , physics , mathematical analysis , thermodynamics
1 pot, 2 stereocenters, 3 components, 4 bonds : An organocatalyzed one‐pot three‐component cascade sequence towards highly substituted indoloquinolizidines in moderate to good yields with excellent enantioselectivities was developed (see scheme). The absolute stereochemistry at C2 and C12 b was created by the organocatalyzed conjugate addition of in situ formed indole‐tethered β‐enaminoesters to α,β‐unsaturated aldehydes, and a subsequent acid‐promoted intramolecular Pictet–Spengler cyclization.