Organocatalytic Michael Addition of Unactivated α-Branched Nitroalkanes to Afford Optically Active Tertiary Nitrocompounds

The direct, asymmetric conjugate addition of unactivated alpha-branched nitroalkanes is developed based on the combined use of chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template to provide tertiary nitrocompounds in 55-80% isolated yields and high enantioselectivity (e....

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Published inOrganic letters Vol. 25; no. 48; pp. 8590 - 8595
Main Authors Lorea, Benat, Garcia-Urricelqui, Ane, Odriozola, Josee M., Razkin, Jesus, Espinal-Viguri, Maialen, Oiarbide, Mikel, Mielgo, Antonia, Garcia, Jesus M., Palomo, Claudio
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 08.12.2023
American Chemical Society
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
ENONES
KETONES
ALKYLATION
DRUGS
CONJUGATE ADDITION
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Summary:The direct, asymmetric conjugate addition of unactivated alpha-branched nitroalkanes is developed based on the combined use of chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template to provide tertiary nitrocompounds in 55-80% isolated yields and high enantioselectivity (e.r. up to 96:4). Elaboration of the ketol moiety in thus obtained adducts allows a fast entry to not only carboxylic and aldehyde derivatives but also nitrile compounds and enantioenriched 5,5-disubstituted gamma-lactams.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03340