Literature DB >> 20229533

C1-symmetric aminosulfoximines in copper-catalyzed asymmetric vinylogous Mukaiyama aldol reactions.

Marcus Frings1, Iuliana Atodiresei, Yutian Wang, Jan Runsink, Gerhard Raabe, Carsten Bolm.   

Abstract

Vinylogous Mukaiyama-type aldol reactions have been catalyzed by a combination of Cu(OTf)2 and readily available C1-symmetric aminosulfoximines. After a fine-tuning of the reaction conditions and an optimization of the modularly assembled ligand structure, high stereoselectivities and excellent yields have been achieved in catalyzed reactions involving various electrophile/nucleophile combinations. The relative and absolute configurations of two products were assigned by X-ray single crystal structure analysis and a comparison of calculated and experimental CD spectra.
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Mukaiyama reaction; aldol reaction; asymmetric catalysis; copper; sulfoximine

Mesh:

Substances:

Year:  2010        PMID: 20229533     DOI: 10.1002/chem.200903077

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  3 in total

Review 1.  Current progress in asymmetric Biginelli reaction: an update.

Authors:  Majid M Heravi; Razieh Moradi; Leyla Mohammadkhani; Borzou Moradi
Journal:  Mol Divers       Date:  2018-06-23       Impact factor: 2.943

Review 2.  Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones.

Authors:  Bin Mao; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Rev       Date:  2017-06-22       Impact factor: 60.622

3.  Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis.

Authors:  Marcus Frings; Isabelle Thomé; Carsten Bolm
Journal:  Beilstein J Org Chem       Date:  2012-09-03       Impact factor: 2.883

  3 in total

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