Literature DB >> 21848304

Introducing a new class of N-phosphoryl ynamides via Cu(I)-catalyzed amidations of alkynyl bromides.

Kyle A DeKorver1, Mary C Walton, Troy D North, Richard P Hsung.   

Abstract

We describe here the first synthesis of N-phosphoryl ynamides featuring C- and P-chirality via copper(I)-catalyzed amidative cross-couplings between phosphoramidates and phosphordiamidates with alkynyl bromides. Also featured is a tandem aza-Claisen-hetero-[2+2] cycloaddition for the synthesis of N-phosphoryl azetidin-2-imines.
© 2011 American Chemical Society

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Year:  2011        PMID： 21848304      PMCID： PMC3170467          DOI： 10.1021/ol201947b

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  28 in total

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  7 in total

1.  An intramolecular [2 + 2] cycloaddition of ketenimines via palladium-catalyzed rearrangements of N-allyl-ynamides.

Authors:  Kyle A DeKorver; Richard P Hsung; Wang-Ze Song; Xiao-Na Wang; Mary C Walton
Journal:  Org Lett       Date:  2012-06-05       Impact factor: 6.005

2.  Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Authors:  Thomas P Willumstad; Olesya Haze; Xiao Yin Mak; Tin Yiu Lam; Yu-Pu Wang; Rick L Danheiser
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3.  Carbocyclization cascades of allyl ketenimines via aza-Claisen rearrangements of N-phosphoryl-N-allyl-ynamides.

Authors:  Kyle A DeKorver; Xiao-Na Wang; Mary C Walton; Richard P Hsung
Journal:  Org Lett       Date:  2012-03-13       Impact factor: 6.005

4.  S3S63 Terminal Ynamides: Synthesis, Coupling Reactions and Additions to Common Electrophiles.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Tetrahedron Lett       Date:  2015-05-06       Impact factor: 2.415

5.  Synthesis of cyclopentenimines from N-allyl ynamides via a tandem aza-Claisen rearrangement-carbocyclization sequence.

Authors:  Xiao-Na Wang; Gabrielle N Winston-McPherson; Mary C Walton; Yu Zhang; Richard P Hsung; Kyle A DeKorver
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6.  Ynamides in ring forming transformations.

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Journal:  Acc Chem Res       Date:  2013-10-28       Impact factor: 22.384

7.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157
  7 in total

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