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Asymmetric Assembly of All‐Carbon Tertiary/Quaternary Nonadjacent Stereocenters through Organocatalytic Conjugate Addition of α‐Cyanoacetates to a Methacrylate Equivalent
Author(s) -
Iriarte Igor,
Vera Silvia,
Badiola Eider,
Mielgo Antonia,
Oiarbide Mikel,
García Jesús M.,
Odriozola José M.,
Palomo Claudio
Publication year - 2016
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.201603082
Subject(s) - stereocenter , enantioselective synthesis , protonation , conjugate , chemistry , michael reaction , quaternary carbon , methacrylate , carbon fibers , base (topology) , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , materials science , polymer , mathematics , copolymer , ion , mathematical analysis , composite number , composite material
An efficient, highly diastereo‐ and enantioselective assembly of acyclic carbonyl fragments possessing nonadjacent all‐carbon tertiary/quaternary stereoarrays is reported based on a Brønsted base catalyzed Michael addition/α‐protonation sequence involving α‐cyanoacetates and 2,4‐dimethyl‐4‐hydroxypenten‐3‐one as novel methacrylate equivalent.