Literature DB >> 18321118

Lewis acid promoted carbon-carbon bond cleavage of gamma-silyloxy-beta-hydroxy-alpha-diazoesters.

Cristian Draghici1, Matthias Brewer.   

Abstract

Cyclic gamma-silyloxy-beta-hydroxy-alpha-diazoesters undergo efficient rupture of the Cbeta-Cgamma bond when treated with tin tetrachloride to provide tethered aldehyde ynoate products in high yield.

Entities:  

Year:  2008        PMID： 18321118     DOI： 10.1021/ja801004d

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


  10 in total

1.  Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations.

Authors:  Sarah E Cleary; Magenta J Hensinger; Zhi-Xin Qin; Xin Hong; Matthias Brewer
Journal:  J Org Chem       Date:  2019-11-20       Impact factor: 4.354

2.  A ring fragmentation approach to medium-sized cyclic 2-alkynones.

Authors:  Nikolay P Tsvetkov; Ali Bayir; Samuel Schneider; Matthias Brewer
Journal:  Org Lett       Date:  2011-12-01       Impact factor: 6.005

3.  Synthesis of demissidine by a ring fragmentation 1,3-dipolar cycloaddition approach.

Authors:  Zhe Zhang; Geoffrey M Giampa; Cristian Draghici; Qiufeng Huang; Matthias Brewer
Journal:  Org Lett       Date:  2013-04-15       Impact factor: 6.005

4.  Stereoelectronic effects in the fragmentation of γ-silyloxy-β-hydroxy-α-diazocarbonyl compounds.

Authors:  Nitinkumar D Jabre; Matthias Brewer
Journal:  J Org Chem       Date:  2012-10-15       Impact factor: 4.354

5.  Formal and total synthesis of (±)-cycloclavine.

Authors:  Nitinkumar D Jabre; Teruki Watanabe; Matthias Brewer
Journal:  Tetrahedron Lett       Date:  2014-01-01       Impact factor: 2.415

6.  Total synthesis of (±)-bisabosqual A.

Authors:  Christopher W am Ende; Zhou Zhou; Kathlyn A Parker
Journal:  J Am Chem Soc       Date:  2012-12-28       Impact factor: 15.419

7.  Fragmentation of bicyclic γ-silyloxy-β-hydroxy-α-diazolactones as an approach to ynolides.

Authors:  Ali Bayir; Matthias Brewer
Journal:  J Org Chem       Date:  2014-06-12       Impact factor: 4.354

8.  Remote C-H insertion of vinyl cations leading to cyclopentenones.

Authors:  Sarah E Cleary; Magenta J Hensinger; Matthias Brewer
Journal:  Chem Sci       Date:  2017-08-03       Impact factor: 9.825

9.  DFT Mechanistic Study of the Cyclopropanation of Styrene and Aryldiazodiacetate Catalyzed by Tris(pentafluorophenyl)borane.

Authors:  Xiuling Wen; Peiquan Lu; Yong Shen; Haojie Peng; Zhuofeng Ke; Cunyuan Zhao
Journal:  ACS Omega       Date:  2022-04-07

10.  A Route to the C,D,E Ring System of the Aspidosperma Alkaloids.

Authors:  Geoffrey M Giampa; Jian Fang; Matthias Brewer
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005
  10 in total

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