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Asymmetric Synthesis of Spiropyrazolones by Sequential Organo‐ and Silver Catalysis
Author(s) -
Hack Daniel,
Dürr Alexander B.,
Deckers Kristina,
Chauhan Pankaj,
Seling Nico,
Rübenach Lukas,
Mertens Lucas,
Raabe Gerhard,
Schoenebeck Franziska,
Enders Dieter
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201510602
Subject(s) - nitroalkene , chemistry , alkyne , stereoselectivity , enantioselective synthesis , catalysis , organocatalysis , reaction mechanism , combinatorial chemistry , organic chemistry
A stereoselective one‐pot synthesis of spiropyrazolones through an organocatalytic asymmetric Michael addition and a formal Conia‐ene reaction has been developed. Depending on the nitroalkene, the 5‐exo‐dig‐cyclization could be achieved by silver‐catalyzed alkyne activation or by oxidation of the intermediate enolate. The mechanistic pathways have been investigated using computational chemistry and mechanistic experiments.