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Enantioselective Addition of Alkynyl Ketones to Nitroolefins Assisted by Brønsted Base/H‐Bonding Catalysis
Author(s) -
Campano Teresa E.,
Iriarte Igor,
Olaizola Olatz,
Etxabe Julen,
Mielgo Antonia,
Ganboa Iñaki,
Odriozola José M.,
García Jesús M.,
Oiarbide Mikel,
Palomo Claudio
Publication year - 2019
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.201805542
Subject(s) - stereocenter , enantioselective synthesis , bifunctional , chemistry , catalysis , adduct , brønsted–lowry acid–base theory , aryl , base (topology) , alkoxy group , organic chemistry , stereochemistry , medicinal chemistry , alkyl , mathematical analysis , mathematics
Various sets of enolizable alkynyl ketones (including methyl ynones with α‐aryl, α‐alkenyl, and α‐alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H‐bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo‐ and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic and polycyclic molecules, including some with intricate carbon skeletons, was also demonstrated.