Literature DB >> 20020697

Preparation of tethered aldehyde ynoates and ynones by ring fragmentation of cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls.

Ali Bayir1, Cristian Draghici, Matthias Brewer.   

Abstract

Cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls undergo Lewis acid induced ring fragmentation to provide either ynoates or ynones tethered to an aldehyde, ketone, or ester. The fragmentation precursors are convenient to prepare by adding lithiated alpha-diazo carbonyls to alpha-oxy ketones. The fragmentation appears general and provides a variety of functional group-rich products in good to excellent yield.

Entities:  

Year:  2010        PMID： 20020697     DOI： 10.1021/jo902405f

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 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.  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

7.  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

Review 8.  Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.

Authors:  Daniil Zhukovsky; Dmitry Dar'in; Olga Bakulina; Mikhail Krasavin
Journal:  Molecules       Date:  2022-03-21       Impact factor: 4.411
  8 in total

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