Literature DB >> 16159267

Tandem aldol-allylation and aldol-aldol reactions with ketone-derived enolsilanes: highly diastereoselective single-step synthesis of complex tertiary carbinols.

Xiaolun Wang1, Qinglin Meng, Nicholas R Perl, Yue Xu, James L Leighton.   

Abstract

A new tandem aldol-allylation reaction employing ketone-derived enolates has been developed that leads to the rapid, diastereoselective synthesis of tertiary carbinol containing fragments with relevance to polyketide natural product synthesis. In addition, the use of ketone-derived enolates has led to the development of a new tandem aldol-aldol reaction.

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Year:  2005        PMID： 16159267     DOI： 10.1021/ja053593s

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


  6 in total

1.  Rapid total syntheses utilizing "supersilyl" chemistry.

Authors:  Brian J Albert; Yousuke Yamaoka; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2011-02-08       Impact factor: 15.336

2.  A triple-aldol cascade reaction for the rapid assembly of polyketides.

Authors:  Brian J Albert; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-01       Impact factor: 15.336

3.  Improved method for the synthesis of beta-carbonyl silyl-1,3-dithianes by the double conjugate addition of 1,3-dithiol to propargylic carbonyl compounds.

Authors:  Sumit Mukherjee; Dimitra Kontokosta; Aditi Patil; Sivakumar Rallapalli; Daesung Lee
Journal:  J Org Chem       Date:  2009-12-04       Impact factor: 4.354

4.  Si-based benzylic 1,4-rearrangement/cyclization reaction.

Authors:  Barry M Trost; Andreas Bertogg
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

5.  An "aprotic" Tamao oxidation/syn-selective tautomerization reaction for the efficient synthesis of the C1-C9 fragment of fludelone.

Authors:  Tyler J Harrison; Philippe M A Rabbat; James L Leighton
Journal:  Org Lett       Date:  2012-09-05       Impact factor: 6.005

6.  Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates.

Authors:  Stephen N Greszler; Jeffrey S Johnson
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005
  6 in total

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