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Enantioselective Construction of Pyrroloindolines Catalyzed by Chiral Phosphoric Acids: Total Synthesis of (−)‐Debromoflustramine B
Author(s) -
Zhang Zuhui,
Antilla Jon C.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201203553
Subject(s) - enantioselective synthesis , phosphoric acid , total synthesis , catalysis , quaternary carbon , chemistry , organic chemistry , amination , combinatorial chemistry
Acids in command : The asymmetric formation of pyrroloindolines with adjacent quaternary and tertiary carbon centers has been achieved through catalysis by a chiral phosphoric acid. Starting from readily available tryptamine, both Michael products and amination products were obtained in high yields and enantioselectivities. The significance of this study was further demonstrated by the total synthesis of (−)‐debromoflustramine B.