Literature DB >> 20161228

A Torquoselective Extrusion of Isoxazoline N-Oxides. Application to the Synthesis of Aryl Vinyl and Divinyl Ketones for Nazarov Cyclization.

Daniel P Canterbury1, Ildiko R Herrick, Joann Um, K N Houk, Alison J Frontier.   

Abstract

A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones.

Entities:  

Year:  2009        PMID： 20161228      PMCID： PMC2703503          DOI： 10.1016/j.tet.2008.10.003

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  19 in total

1.  Recent advances in the Baylis-Hillman reaction and applications.

Authors:  Deevi Basavaiah; Anumolu Jaganmohan Rao; Tummanapalli Satyanarayana
Journal:  Chem Rev       Date:  2003-03       Impact factor: 60.622

2.  Origins of inward torquoselectivity by silyl groups and other sigma-acceptors in electrocyclic reactions of cyclobutenes.

Authors:  Patrick S Lee; Xiyun Zhang; K N Houk
Journal:  J Am Chem Soc       Date:  2003-04-30       Impact factor: 15.419

3.  Theoretical investigation of the stereoselective stepwise cope rearrangement of a 3-vinylmethylenecyclobutane.

Authors:  Yi-Lei Zhao; Christopher P Suhrada; Michael E Jung; K N Houk
Journal:  J Am Chem Soc       Date:  2006-08-30       Impact factor: 15.419

4.  Dicobalt octacarbonyl promoted rearrangement of 4-isoxazolines to acylaziridines: dramatic rate acceleration with very high substrate tolerance.

Authors:  Teruhiko Ishikawa; Takayuki Kudoh; Juri Yoshida; Ayako Yasuhara; Shinobu Manabe; Seiki Saito
Journal:  Org Lett       Date:  2002-05-30       Impact factor: 6.005

5.  Combined computational and experimental studies of the mechanism and scope of the retro-Nazarov reaction.

Authors:  Michael Harmata; Peter R Schreiner; Dong Reyoul Lee; Patrick L Kirchhoefer
Journal:  J Am Chem Soc       Date:  2004-09-08       Impact factor: 15.419

6.  Polarizing the Nazarov cyclization: the impact of dienone substitution pattern on reactivity and selectivity.

Authors:  Wei He; Ildiko R Herrick; Tulay A Atesin; Patrick A Caruana; Colleen A Kellenberger; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2008-01-23       Impact factor: 15.419

7.  An orbital phase theory for the torquoselectivity of the ring-opening reactions of 3-substituted cyclobutenes: geminal bond participation.

Authors:  Mikihito Yasui; Yuji Naruse; Satoshi Inagaki
Journal:  J Org Chem       Date:  2004-10-15       Impact factor: 4.354

8.  Synthesis of alpha-acyl-functionalized azacycles by Pd-catalyzed cross-coupling reactions of alpha-alkoxyboronates with lactam-derived vinyl triflates.

Authors:  Ernesto G Occhiato; Cristina Prandi; Alessandro Ferrali; Antonio Guarna; Annamaria Deagostino; Paolo Venturello
Journal:  J Org Chem       Date:  2002-10-04       Impact factor: 4.354

9.  Improved yields with added copper(I) salts in carbonylative stille couplings of sterically hindered vinylstannanes.

Authors:  R D Mazzola; Sören Giese; Chantel L Benson; F G West
Journal:  J Org Chem       Date:  2004-01-09       Impact factor: 4.354

10.  Polarizing the Nazarov cyclization: efficient catalysis under mild conditions.

Authors:  Wei He; Xiufeng Sun; Alison J Frontier
Journal:  J Am Chem Soc       Date:  2003-11-26       Impact factor: 15.419
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  6 in total

1.  Formal synthesis of (+/-)-roseophilin.

Authors:  Abdallah Y Bitar; Alison J Frontier
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

2.  Synthesis of (±)-tetrapetalone A-Me aglycon.

Authors:  Peter N Carlsen; Tyler J Mann; Amir H Hoveyda; Alison J Frontier
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-07       Impact factor: 15.336

3.  Studies toward the AB ring system of the tetrapetalone natural products.

Authors:  Peter Carlsen; Chao Jiang; Ildiko R Herrick; Alison J Frontier
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

4.  Photoassisted access to complex polyheterocycles containing a β-lactam moiety.

Authors:  Weston J Umstead; Olga A Mukhina; Andrei G Kutateladze
Journal:  J Photochem Photobiol A Chem       Date:  2016-07-07       Impact factor: 4.291

5.  Photoinduced Cycloadditions in the Diversity-Oriented Synthesis Toolbox: Increasing Complexity with Straightforward Postphotochemical Modifications.

Authors:  Weston J Umstead; Olga A Mukhina; N N Bhuvan Kumar; Andrei G Kutateladze
Journal:  Aust J Chem       Date:  2015-07-24       Impact factor: 1.321

6.  Synthesis of spirocyclic Δ4-isoxazolines via [3 + 2] cycloaddition of indanone-derived ketonitrones with alkynes.

Authors:  Yilin Liu; Jiaxue Liu; Yan-Yun Liu; Boxiao Tang; Hongwei Lin; Yuanxiang Li; Lin Zhang
Journal:  RSC Adv       Date:  2021-09-13       Impact factor: 3.361
  6 in total

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