Literature DB >> 29694690

Pd-Catalyzed Selective Remote Ring Opening of Polysubstituted Cyclopropanols.

Sukhdev Singh1, Marwan Simaan1, Ilan Marek1.   

Abstract

The distant functionalization of ω-ene cyclopropanols is induced by a Pd-catalyzed Heck reaction triggering a "metal-walk" and selective ring-opening of the three-membered ring. This approach provides a new class of acyclic aldehydes possessing concomitantly a stereodefined double bond and a quaternary carbon stereocenter α to the carbonyl group.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cyclopropanol; metal walk; quaternary stereocenters; remote functionalization; stereochemistry

Year:  2018        PMID: 29694690     DOI: 10.1002/chem.201802016

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


  5 in total

1.  Rate Profiling the Impact of Remote Functional Groups on the Redox-Relay Heck Reaction.

Authors:  Samantha L Kraus; Sean P Ross; Matthew S Sigman
Journal:  Org Lett       Date:  2021-03-12       Impact factor: 6.005

2.  Development and Mechanistic Interrogation of Interrupted Chain-Walking in the Enantioselective Relay Heck Reaction.

Authors:  Sean P Ross; Ajara A Rahman; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2020-05-29       Impact factor: 15.419

3.  Mechanistic Insights on the Selectivity of the Tandem Heck-Ring-Opening of Cyclopropyldiol Derivatives.

Authors:  Anthony Cohen; Alexander Kaushansky; Ilan Marek
Journal:  JACS Au       Date:  2022-03-05

4.  Stereoselective tandem iridium-catalyzed alkene isomerization-cope rearrangement of ω-diene epoxides: efficient access to acyclic 1,6-dicarbonyl compounds.

Authors:  Rahul Suresh; Itai Massad; Ilan Marek
Journal:  Chem Sci       Date:  2021-06-09       Impact factor: 9.825

Review 5.  Stereoselective Remote Functionalization via Palladium-Catalyzed Redox-Relay Heck Methodologies.

Authors:  Holly E Bonfield; Damien Valette; David M Lindsay; Marc Reid
Journal:  Chemistry       Date:  2020-10-08       Impact factor: 5.236

  5 in total

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