Premium
Stereoselective Synthesis of Chiral Polycyclic Indolic Architectures through Pd 0 ‐Catalyzed Tandem Deprotection/Cyclization of Tetrahydro‐β‐carbolines on Allenes
Author(s) -
Gobé Valérian,
Guinchard Xavier
Publication year - 2015
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.201500273
Subject(s) - allene , regioselectivity , chemistry , tandem , stereoselectivity , catalysis , pictet–spengler reaction , phosphoric acid , cascade reaction , diastereomer , stereochemistry , combinatorial chemistry , organic chemistry , materials science , composite material
Enantioenriched N ‐allyl tetrahydro‐β‐carbolines were prepared by chiral phosphoric acid‐catalyzed Pictet–Spengler reactions. The compounds undergo Pd 0 ‐catalyzed cyclizations through a tandem deprotection/cyclization process. The regioselectivity of the attack is controlled by the chain length and by the substitution pattern of the allene function. Products resulting from 5‐ exo ‐ or 6‐ exo ‐attack were obtained with diastereoisomeric ratio up to 95:5. Azepinopyrrido[3,4‐ b ]indoles were obtained by 7‐ endo ‐cyclizations.