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Literature DB >> 25768436

Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Travis C McMahon¹, Jose M Medina¹, Yun-Fang Yang¹, Bryan J Simmons¹, K N Houk¹, Neil K Garg¹.

Abstract

We report the generation of the first 3,4-piperidyne and its use as a building block for the synthesis of annulated piperidines. Experimental and computational studies of this intermediate are disclosed, along with comparisons to the well-known 3,4-pyridyne. The distortion/interaction model is used to explain the observed regioselectivities.

Entities: Chemical Disease Gene Species

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Year: 2015 PMID： 25768436 PMCID： PMC4502428 DOI： 10.1021/jacs.5b01589

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

24 in total

Review 1. A comprehensive history of arynes in natural product total synthesis.

Authors: Pamela M Tadross; Brian M Stoltz
Journal: Chem Rev Date: 2012-03-23 Impact factor: 60.622

2. Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes.

Authors: Anup Bhunia; Santhivardhana Reddy Yetra; Akkattu T Biju
Journal: Chem Soc Rev Date: 2012-01-26 Impact factor: 54.564

3. Synthesis and kinetic analysis of the N-acetylhexosaminidase inhibitor XylNAc-isofagomine.

Authors: Spencer Knapp; Chunhua Yang; Srihari Pabbaraja; Brian Rempel; Steven Reid; Stephen G Withers
Journal: J Org Chem Date: 2005-09-16 Impact factor: 4.354

4. Arynes and cyclohexyne in natural product synthesis.

Authors: Christian M Gampe; Erick M Carreira
Journal: Angew Chem Int Ed Engl Date: 2012-03-15 Impact factor: 15.336

5. A five-step synthesis of (S)-macrostomine from (S)-nicotine.

Authors: Monica F Enamorado; Pauline W Ondachi; Daniel L Comins
Journal: Org Lett Date: 2010-10-15 Impact factor: 6.005

6. Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

Authors: G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal: J Am Chem Soc Date: 2010-11-29 Impact factor: 15.419

7. N-tosyl-3-azacyclohexyne. Synthesis and chemistry of a strained cyclic ynamide.

Authors: Sami F Tlais; Rick L Danheiser
Journal: J Am Chem Soc Date: 2014-10-22 Impact factor: 15.419

8. Escape from flatland: increasing saturation as an approach to improving clinical success.

Authors: Frank Lovering; Jack Bikker; Christine Humblet
Journal: J Med Chem Date: 2009-11-12 Impact factor: 7.446

9. Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

Authors: Adam E Goetz; Neil K Garg
Journal: Nat Chem Date: 2012-11-25 Impact factor: 24.427

10. Cycloadditions of cyclohexynes and cyclopentyne.

Authors: Jose M Medina; Travis C McMahon; Gonzalo Jiménez-Osés; K N Houk; Neil K Garg
Journal: J Am Chem Soc Date: 2014-10-10 Impact factor: 15.419

15 in total

1. Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

Authors: Expédite Yen-Pon; Pier Alexandre Champagne; Lucie Plougastel; Sandra Gabillet; Pierre Thuéry; Mizuki Johnson; Gilles Muller; Grégory Pieters; Frédéric Taran; K N Houk; Davide Audisio
Journal: J Am Chem Soc Date: 2019-01-15 Impact factor: 15.419

Generation and regioselective trapping of a 3,4-piperidyne for the synthesis of functionalized heterocycles.

Review 1. A comprehensive history of arynes in natural product total synthesis.

2. Recent advances in transition-metal-free carbon-carbon and carbon-heteroatom bond-forming reactions using arynes.

3. Synthesis and kinetic analysis of the N-acetylhexosaminidase inhibitor XylNAc-isofagomine.

4. Arynes and cyclohexyne in natural product synthesis.

5. A five-step synthesis of (S)-macrostomine from (S)-nicotine.

6. Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

7. N-tosyl-3-azacyclohexyne. Synthesis and chemistry of a strained cyclic ynamide.

8. Escape from flatland: increasing saturation as an approach to improving clinical success.

9. Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

10. Cycloadditions of cyclohexynes and cyclopentyne.

1. Sydnone-Based Approach to Heterohelicenes through 1,3-Dipolar-Cycloadditions.

2. Synthesis of Cyclic β-Silylalkenyl Triflates via an Alkenyl Cation Intermediate.

3. Diels-Alder cycloadditions of strained azacyclic allenes.

4. Quantification of the Electrophilicity of Benzyne and Related Intermediates.

5. Concise Approach to Cyclohexyne and 1,2-Cyclohexadiene Precursors.

6. Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

7. Nitrone Cycloadditions of 1,2-Cyclohexadiene.

8. Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.

9. Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds.

10. Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.