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Literature DB >> 29910538

Facile Synthesis of 3-Amido-Dienynes via a Tandem α-Propargylation-Isomerization of Chiral Allenamides and their Applications in Diels-Alder Cycloadditions.

Zhi-Xiong Ma¹, Li-Chao Fang¹, Richard P Hsung¹.

Abstract

A series of de novo 3-amido-dienynes was synthesized via tandem α-propargylation-isomerization of chiral allenamides with moderate E/Z ratio. Reactivities of E-and Z-isomers were examined.

Entities: Chemical Gene

Keywords: 3-amido-dienyne; Diels-Alder reaction; allenamide; propargylation; tandem

Year: 2017 PMID： 29910538 PMCID： PMC6000824 DOI： 10.1055/s-0036-1590899

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

16 in total

1. A tandem 1,3-H-shift-6π-electrocyclization-cyclic 2-amido-diene intramolecular Diels-Alder cycloaddition approach to BCD-Ring of atropurpuran.

Authors: Ryuji Hayashi; Zhi-Xiong Ma; Richard P Hsung
Journal: Org Lett Date: 2011-12-13 Impact factor: 6.005

2. Acceleration of conjugated dienyne cycloaromatization.

Authors: David M Hitt; Joseph M O'Connor
Journal: Chem Rev Date: 2011-10-06 Impact factor: 60.622

3. Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors: Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal: Org Lett Date: 2010-11-19 Impact factor: 6.005

4. A highly stereoselective Diels-Alder cycloaddition of enones with chiral cyclic 2-amidodienes derived from allenamides.

Authors: Li-Chao Fang; Richard P Hsung; Zhi-Xiong Ma; William R Presser
Journal: Org Lett Date: 2013-09-03 Impact factor: 6.005

5. Total synthesis of (±)-γ-lycorane via the electrocyclic ring closure of a divinylpyrroline.

Authors: Raymond J Huntley; Raymond L Funk
Journal: Tetrahedron Lett Date: 2011-12-14 Impact factor: 2.415

6. Regio- and stereoselective isomerizations of allenamides: synthesis of 2-amido-dienes and their tandem isomerization-electrocyclic ring-closure.

Authors: Ryuji Hayashi; Richard P Hsung; John B Feltenberger; Andrew G Lohse
Journal: Org Lett Date: 2009-05-21 Impact factor: 6.005

Review 7. Allenamides: a powerful and versatile building block in organic synthesis.

Authors: Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal: Chem Rev Date: 2013-04-04 Impact factor: 60.622

8. An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors: Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal: Beilstein J Org Chem Date: 2011-04-07 Impact factor: 2.883