Premium
General and Efficient Organocatalytic Synthesis of Indoloquinolizidines, Pyridoquinazolines and Quinazolinones through a One‐Pot Domino Michael Addition‐Cyclization‐ Pictet–Spengler or 1,2‐Amine Addition Reaction
Author(s) -
Rueping Magnus,
Volla Chandra M. R.,
Bolte Michael,
Raabe Gerhard
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100258
Subject(s) - chemistry , michael reaction , tryptamine , diastereomer , domino , organocatalysis , substrate (aquarium) , amine gas treating , nucleophile , cascade reaction , combinatorial chemistry , addition reaction , nucleophilic addition , organic chemistry , enantioselective synthesis , catalysis , biochemistry , oceanography , geology
An asymmetric organocatalyzed reaction sequence involving a Michael addition of various 1,3‐dicarbonyl compounds to α,β‐unsaturated aldehydes with subsequent diastereoselective Pictet–Spengler cyclization has been developed. The substrate scope was found to be general and optically active indoloquinolizidines were isolated as single diastereomers in high yields with high to excellent enantioselectivites. In addition to tryptamine, the reaction has also been successfully applied to other nucleophiles including o ‐aminobenzylamine and anthranilamide giving rise to pyridoquinauolines and quinazolinones.