Literature DB >> 23496162

Synthesis of functionalized allenamides from ynamides by enolate Claisen rearrangement.

Julien Brioche1, Christophe Meyer, Janine Cossy.   

Abstract

The Claisen rearrangement of N-Boc glycinates derived from ynamido-alcohols affords an efficient and stereoselective access to highly functionalized allenamides. These compounds undergo silver-catalyzed cyclization to 3-pyrrolines which are useful precursors for the synthesis of substituted pyrrolidines.

Entities:  

Year:  2013        PMID： 23496162     DOI： 10.1021/ol400402n

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


  10 in total

1.  SYNTHESIS OF DE NOVO CHIRAL γ-AMINO-YNAMIDES USING LITHIATED YNAMIDES. OBSERVATION OF A UNIQUE 5-ENDO-DIG CYCLIZATION WITH AN INVERSION OF S-CENTER.

Authors:  Xiao-Na Wang; Richard P Hsung; Sierra K Fox; Ming-Can Lv; Rui Qi
Journal:  Heterocycles       Date:  2014-01-01       Impact factor: 0.831

2.  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
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

3.  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

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

Authors:  Xiao-Na Wang; Richard P Hsung; Rui Qi; Sierra K Fox; Ming-Can Lv
Journal:  Org Lett       Date:  2013-05-06       Impact factor: 6.005

5.  A Simple Procedure for the Synthesis of β-Hydroxyallenamides via Homoallenylation of Aldehydes.

Authors:  Byeong-Seon Kim; Osvaldo Gutierrez; Marisa C Kozlowski; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2018-01-30       Impact factor: 5.837

Review 6.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

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

8.  Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.

Authors:  Jian-Siang Poh; Szabolcs Makai; Timo von Keutz; Duc N Tran; Claudio Battilocchio; Patrick Pasau; Steven V Ley
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-11       Impact factor: 15.336

Review 9.  Metal-mediated synthesis of pyrrolines.

Authors:  Noelia S Medran; Agustina La-Venia; Sebastian A Testero
Journal:  RSC Adv       Date:  2019-02-27       Impact factor: 4.036

10.  Synthesis of 3-Amino-1-benzothiophene-1,1-diones by Alkyne Directed Hydroarylation and 1/N→3/C-Sulfonyl Migration.

Authors:  Ivan Bernar; Daniel Blanco-Ania; Sophie J Stok; Lia Sotorríos; Enrique Gómez-Bengoa; Floris P J T Rutjes
Journal:  European J Org Chem       Date:  2018-10-10
  10 in total

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