Publication: Organocatalytic Michael addition of unactivated a-branched nitroalkanes to afford optically active tertiary nitrocompounds
Consultable a partir de
Date
2023
Authors
Lorea Revilla, Beñat
García-Urricelqui, Ane
Razkin Lizarraga, Jesús
Oiarbide, Mikel
Mielgo, Antonia
Palomo, Claudio
Director
Publisher
ACS
Acceso abierto / Sarbide irekia
Artículo / Artikulua
Versión publicada / Argitaratu den bertsioa
Project identifier
AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-109633GB-C22/ES/
/PID2022-137153NB-C21
/PID2022-137153NB-C21
Abstract
The direct, asymmetric conjugate addition of unactivated ¿-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 ¿-lactams.
Keywords
Department
Ciencias / Zientziak / Institute for Advanced Materials and Mathematics - INAMAT2
Faculty/School
Degree
Doctorate program
Editor version
Funding entities
The authors thank the Basque Government (EJ, grant IT1583-22) and
Agencia Estatal de Investigación (grants PID2019-109633GB
and PID2022-137153NB-C21/AEI/10.13039/501100011033)
for financial support. A.G.-U. thanks EJ; B.L. thanks the
Navarra Government, and M.E.-V. thanks UPNA (PJUPNA18-
2022).
© 2023 The Authors. This article is licensed under CC-BY 4.0.
Los documentos de Academica-e están protegidos por derechos de autor con todos los derechos reservados, a no ser que se indique lo contrario.