Literature DB >> 24307550

α,β-Unsaturated acyl cyanides as new bis-electrophiles for enantioselective organocatalyzed formal [3+3]spiroannulation.

Sébastien Goudedranche1, Xavier Bugaut, Thierry Constantieux, Damien Bonne, Jean Rodriguez.   

Abstract

α,β-Unsaturated acyl cyanides are key bis-electrophile substrates for successful domino enantioselective organocatalyzed Michael-intramolecular acylation domino sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4,5]decanone ring systems by a formal [3+3]spiroannulation, constituting a rare example of synthesis of glutarimides in an optically active form.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  domino reactions; enantioselectivity; glutarimides; organocatalysis; spiroannulation

Year:  2013        PMID: 24307550     DOI: 10.1002/chem.201303613

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


  7 in total

1.  Benchmark DFT studies on C-CN homolytic cleavage and screening the substitution effect on bond dissociation energy.

Authors:  Naveen Kosar; Khurshid Ayub; Mazhar Amjad Gilani; Tariq Mahmood
Journal:  J Mol Model       Date:  2019-01-28       Impact factor: 1.810

2.  Enantioselective Diels-Alder-lactamization organocascades employing a furan-based diene.

Authors:  Mikail E Abbasov; Brandi M Hudson; Weixu Kong; Dean J Tantillo; Daniel Romo
Journal:  Org Biomol Chem       Date:  2017-04-11       Impact factor: 3.876

Review 3.  Recent synthetic strategies toward the synthesis of spirocyclic compounds comprising six-membered carbocyclic/heterocyclic ring systems.

Authors:  Kashaf Babar; Ameer Fawad Zahoor; Sajjad Ahmad; Rabia Akhtar
Journal:  Mol Divers       Date:  2020-07-21       Impact factor: 2.943

4.  Enantioselective Stereodivergent Nucleophile-Dependent Isothiourea-Catalysed Domino Reactions.

Authors:  Anastassia Matviitsuk; James E Taylor; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chemistry       Date:  2016-10-11       Impact factor: 5.236

5.  Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis.

Authors:  Mark D Greenhalgh; Shen Qu; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chem Sci       Date:  2018-05-04       Impact factor: 9.825

6.  Asymmetric Synthesis of a 5,6,7,8-Tetrahydro-1,6-naphthyridine Scaffold Leading to Potent Retinoid-Related Orphan Receptor γt Inverse Agonist TAK-828F.

Authors:  Ryoji Tsuruoka; Naoki Yoshikawa; Takahiro Konishi; Mitsuhisa Yamano
Journal:  J Org Chem       Date:  2020-07-23       Impact factor: 4.354

7.  Non-bonding 1,5-S···O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles.

Authors:  Emily R T Robinson; Daniel M Walden; Charlene Fallan; Mark D Greenhalgh; Paul Ha-Yeon Cheong; Andrew D Smith
Journal:  Chem Sci       Date:  2016-07-04       Impact factor: 9.825

  7 in total

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