Literature DB >> 21739977

Combined C-H functionalization/Cope rearrangement with vinyl ethers as a surrogate for the vinylogous Mukaiyama aldol reaction.

Yajing Lian1, Huw M L Davies.   

Abstract

Vinyl ethers selectively undergo the combined C-H functionalization/Cope rearrangement reaction via an s-cis/boat transition state. With chiral dirhodium catalysts, products are generated in a highly diastereoselective and enantioselective fashion. This reaction can be considered as a surrogate to the traditional vinylogous Mukaiyama aldol reaction. Effective kinetic resolution has been achieved, leading to the recovery of a cyclic vinyl ether with axial chirality of high enantiomeric purity.
© 2011 American Chemical Society

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Year:  2011        PMID： 21739977      PMCID： PMC3314713          DOI： 10.1021/ja2051155

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  47 in total

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7.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

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8.  The combined C-H functionalization/Cope rearrangement: discovery and applications in organic synthesis.

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Journal:  Acc Chem Res       Date:  2012-05-11       Impact factor: 22.384

9.  Synthesis of complex hexacyclic compounds via a tandem Rh(II)-catalyzed double-cyclopropanation/Cope rearrangement/Diels-Alder reaction.

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Review 10.  Recent advances in C(sp(3))-H bond functionalization via metal-carbene insertions.

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