AI Article Synopsis

  • A chromium-catalyzed process was developed to create bromocyclopropanes from alkenes using bromoform as the reactant.
  • An organosilicon compound was crucial for reducing chromium and producing a reactive bromomethylidene-chromium(iii) species necessary for the reaction.
  • This cyclopropanation method effectively worked with different types of alkenes, including allyl ethers, allyl esters, and both terminal and cyclic alkenes.

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Catalytic Diastereo- and Enantioselective Cyclopropanation of gem-Dihaloalkanes and Terminal Olefins.

Angew Chem Int Ed Engl

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Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science, Westlake University, Hangzhou, 310024, China.

Chiral cyclopropane derivatives are essential in synthetic chemistry and drug discovery. Their synthesis commonly relies on asymmetric cyclopropanation of diazo compounds, potentially explosive and needing stabilizing substituents. Thus, asymmetric catalytic transformations of non-stabilized carbenes or carbenoids remain a formidable challenge.

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Article Synopsis
  • A chromium-catalyzed process was developed to create bromocyclopropanes from alkenes using bromoform as the reactant.
  • An organosilicon compound was crucial for reducing chromium and producing a reactive bromomethylidene-chromium(iii) species necessary for the reaction.
  • This cyclopropanation method effectively worked with different types of alkenes, including allyl ethers, allyl esters, and both terminal and cyclic alkenes.
View Article and Find Full Text PDF

Chromium-catalyzed homoaldol equivalent reaction employing a nucleophilic propenyl acetate.

J Am Chem Soc

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Texas A&M University, Department of Chemistry, P.O. Box 30012, College Station, Texas 77842-3012, USA.

A scalable, highly regioselective chromium-catalyzed homoaldol equivalent reaction employing 3-bromopropenyl acetate as a masked homoenolate nucleophile in additions to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes under mild Cr/Mn redox conditions in good to excellent yields is reported. The resulting vinyl acetate-containing adducts are easily hydrolyzed with mild base to provide formal homoaldol adducts, or transformed to other more functionalized products by stereoselective transformations including epoxidation and cyclopropanation.

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