Literature DB >> 18798638

Origins of stereoselectivity in the oxido-alkylidenation of alkynes.

Daniel P Canterbury1, Alison J Frontier, Joann M Um, Paul H-Y Cheong, Dahlia A Goldfeld, Richard A Huhn, K N Houk.   

Abstract

A mild, convenient oxido-alkylidenation of alkynes is described. The three-step sequence involves the 1,3-dipolar cycloaddition of a nitrone and an alkynoate, oxidation of the resulting isoxazoline, and stereoselective extrusion of nitrosomethane. Quantum mechanical calculations identified the interactions of R3 with the oxidant and the preferred conformation of a diradical intermediate as major factors controlling the stereoselectivity of the oxidation and torquoselectivity of the extrusion.

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Year:  2008        PMID： 18798638      PMCID： PMC2662994          DOI： 10.1021/ol8019154

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


  15 in total

1.  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

2.  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

3.  Sulfoxide-induced stereoselection in [1,5]-sigmatropic hydrogen shifts of vinylallenes. A computational study.

Authors:  Olalla Nieto Faza; Carlos Silva López; Angel R de Lera
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

4.  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

5.  Diels-Alder and ene reactions of singlet oxygen, nitroso compounds and triazolinediones: transition states and mechanisms from contemporary theory.

Authors:  Andrew G Leach; K N Houk
Journal:  Chem Commun (Camb)       Date:  2002-06-21       Impact factor: 6.222

6.  Theoretical study of the electrocyclic ring closure of hydroxypentadienyl cations.

Authors:  Olalla Nieto Faza; Carlos Silva López; Rosana Alvarez; Angel R de Lera
Journal:  Chemistry       Date:  2004-09-06       Impact factor: 5.236

7.  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

8.  Theoretical study of the vinyl allene oxide to cyclopent-2-en-1-one rearrangement: mechanism, torquoselectivity and solvent effects.

Authors:  Carlos Silva López; Olalla Nieto Faza; Darrin M York; Angel R de Lera
Journal:  J Org Chem       Date:  2004-05-28       Impact factor: 4.354

9.  Thermal decomposition of meso- and d,l-3,4-diethyl-3,4-dimethyldiazetine N,N'-dioxide.

Authors:  Gary W Breton; Justine E Nickerson; Anna M Greene; Lindsey H Oliver
Journal:  Org Lett       Date:  2007-07-14       Impact factor: 6.005

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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  4 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.  Electrospray ionization (ESI) fragmentations and dimethyldioxirane reactivities of three diverse lactams having full, half, and zero resonance energies.

Authors:  Kathleen M Morgan; David J Ashline; Jessica P Morgan; Arthur Greenberg
Journal:  J Org Chem       Date:  2013-12-30       Impact factor: 4.354

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

Authors:  Daniel P Canterbury; Ildiko R Herrick; Joann Um; K N Houk; Alison J Frontier
Journal:  Tetrahedron       Date:  2009-04-18       Impact factor: 2.457
  4 in total

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