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A New Imidazole‐Containing Imidazolidinone Catalyst for Organocatalyzed Asymmetric Conjugate Addition of Nitroalkanes to Aldehydes
Author(s) -
Hojabri Leila,
Hartikka Antti,
Moghaddam Firouz Matloubi,
Arvidsson Per I.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600316
Subject(s) - chemistry , iminium , michael reaction , organocatalysis , enantioselective synthesis , imidazole , amine gas treating , addition reaction , organic chemistry , catalysis , conjugate , enantiomer , combinatorial chemistry , mathematical analysis , mathematics
Herein we report a new organocatalyst for the asymmetric Michael addition of nitroalkanes to α,β‐unsaturated aldehydes. This catalyst incorporates a basic imidazole group in addition to the secondary amine responsible for activation of the α,β‐unsaturated carbonyl compounds via iminium ion formation. The new organocatalyst is capable of catalyzing the enantioselective carbon‐carbon bond formation with a high degree of enantiocontrol providing products in enantiomeric excesses of up to 92 % and yields of up to to 91 %. These results constitute the best results so far reported for organocatalyzed Michael additions of nitroalkanes to α,β‐unsaturated aldehydes, and provide proof of principle that organocatalysts incorporating two internal basic moieties may find broad application in organocatalyzed Michael additions.