Literature DB >> 12917006

Use of hindered silyl ethers as protecting groups for the non-aldol aldol process.

Michael E Jung1, Barbara Hoffmann, Bernhard Rausch, Jean-Marie Contreras.   

Abstract

[reaction: see text] Bulky epoxy bis-silyl ethers, e.g., 15, derived from 5-trialkylsilyloxy-2-alken-1-ols by epoxidation and silylation were treated with TMSOTf to afford non-aldol aldol rearrangement products, the 3,5-bis(silyloxy)alkanals, e.g., 16, with little to none of the corresponding tetrahydrofurans.

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Year:  2003        PMID： 12917006     DOI： 10.1021/ol035295a

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


  4 in total

1.  Computational elucidation of the origins of reactivity and selectivity in non-aldol aldol rearrangements of cyclic epoxides.

Authors:  Hao Wang; K N Houk; Damian A Allen; Michael E Jung
Journal:  Org Lett       Date:  2011-05-13       Impact factor: 6.005

2.  Total synthesis of auripyrone B using a non-aldol aldol-cuprate opening process.

Authors:  Michael E Jung; Manon Chaumontet; Ramin Salehi-Rad
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

3.  Total synthesis of auripyrone A using a tandem non-aldol aldol/Paterson aldol process as a key step.

Authors:  Michael E Jung; Ramin Salehi-Rad
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.

Authors:  Arun K Ghosh; Khriesto Shurrush; Sarang Kulkarni
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354
  4 in total

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