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A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins – A Concise Total Synthesis of Antitumor Agents
Author(s) -
Subba Reddy Ummareddy Venkata,
Chennapuram Madhu,
Seki Kento,
Seki Chigusa,
Anusha Bheemreddy,
Kwon Eunsang,
Okuyama Yuko,
Uwai Koji,
Tokiwa Michio,
Takeshita Mitsuhiro,
Nakano Hiroto
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700399
Subject(s) - enantioselective synthesis , chemistry , isatin , aldol reaction , catalysis , acetaldehyde , alcohol , organic chemistry , combinatorial chemistry , stereochemistry , ethanol
Enantioselective crossed aldol reactions of isatin derivatives and acetaldehyde have been developed with a series of simple diamino alcohol catalysts to afford 3‐substituted 3‐hydroxyindolin‐2‐ones in high chemical yields (up to 95 %) and optical purities (up to 92 % ee ). The synthetic potential of the present protocol has been demonstrated by concise, enantioselective, protecting‐group‐free, and transition metal‐free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC‐1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible transition states.