Literature DB >> 30294820

Versatility in the Brook Rearrangement for the Selective Ring-Opening of Three-Membered Rings.

Coralie Tugny1, Fa-Guang Zhang1, Ilan Marek1.   

Abstract

From a single α-silylated carbinol intermediate, easily accessible by carbometallation of cyclopropenes, various scaffolds featuring a quaternary carbon stereocenter could be obtained selectively. The selectivity towards these different products was achieved by either changing the experimental conditions or the nature of the organometallic species involved.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brook rearrangement; cyclopropane; fragmentation; quaternary carbon; selectivity

Year:  2018        PMID: 30294820     DOI: 10.1002/chem.201805006

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


  3 in total

1.  Diastereoselective ring opening of fully-substituted cyclopropanes via intramolecular Friedel-Crafts alkylation.

Authors:  Veeranjaneyulu Lanke; Fa-Guang Zhang; Alexander Kaushansky; Ilan Marek
Journal:  Chem Sci       Date:  2019-08-27       Impact factor: 9.825

2.  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

3.  Regio- and Diastereoselective Carbometalation Reaction of Cyclopropenes.

Authors:  Yair Cohen; Ilan Marek
Journal:  Acc Chem Res       Date:  2022-09-14       Impact factor: 24.466

  3 in total

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