Literature DB >> 23646900

A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.

Xiao-Na Wang1, Richard P Hsung, Rui Qi, Sierra K Fox, Ming-Can Lv.   

Abstract

A highly diastereoselective addition of lithiated ynamides to Ellman-Davis chiral imines is described. While additions of N-sulfonyl ynamides are highly stereoselective even without Lewis acids, the use of BF3-OEt2 completely reversed the stereoselectivity. In addition, oxazolidinone-substituted ynamides behaved differently and functioned better with BF3-OEt2, and the chirality of the oxazolidinone ring exerts no impact on the selectivity.

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Year:  2013        PMID： 23646900      PMCID： PMC3759603          DOI： 10.1021/ol400989x

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


  49 in total

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7.  Synthesis of functionalized allenamides from ynamides by enolate Claisen rearrangement.

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Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

8.  Ag- and Au-catalyzed addition of alcohols to ynimides: β-regioselective carbonylation and production of oxazoles.

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9.  Highly diastereoselective addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl aldimines: a practical and general access to chiral alpha-branched amines.

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Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354

10.  Platinum-catalyzed oxoarylations of ynamides with nitrones.

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  5 in total

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

3.  Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Chem Commun (Camb)       Date:  2014-02-12       Impact factor: 6.222

4.  Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides.

Authors:  Andrea M Cook; Christian Wolf
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-25       Impact factor: 15.336

5.  Ynamides in ring forming transformations.

Authors:  Xiao-Na Wang; Hyun-Suk Yeom; Li-Chao Fang; Shuzhong He; Zhi-Xiong Ma; Brant L Kedrowski; Richard P Hsung
Journal:  Acc Chem Res       Date:  2013-10-28       Impact factor: 22.384
  5 in total

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