Literature DB >> 22296255

Diastereoselective construction of syn-1,3-dioxanes via a bismuth-mediated two-component hemiacetal/oxa-conjugate addition reaction.

P Andrew Evans1, Aleksandr Grisin, Michael J Lawler.   

Abstract

The bismuth-mediated two-component hemiacetal/oxa-conjugate addition of δ-trialkylsilyloxy and δ-hydroxy α,β-unsaturated aldehydes and ketones with alkyl aldehydes provides the syn-1,3-dioxanes in a highly efficient and stereoselective manner. The key advantages of this protocol are its operational simplicity and its ability to directly access electron-withdrawing groups without recourse to oxidation state adjustments.

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Year:  2012        PMID: 22296255     DOI: 10.1021/ja208668u

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


  8 in total

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Journal:  Chem Soc Rev       Date:  2018-06-18       Impact factor: 54.564

2.  Total synthesis of marinomycin A using salicylate as a molecular switch to mediate dimerization.

Authors:  P Andrew Evans; Mu-Hua Huang; Michael J Lawler; Sergio Maroto
Journal:  Nat Chem       Date:  2012-07-01       Impact factor: 24.427

3.  Stereoselective Synthesis of Dioxolanes and Oxazolidines via a Desymmetrization Acetalization/Michael Cascade.

Authors:  David M Rubush; Tomislav Rovis
Journal:  Synlett       Date:  2014-03       Impact factor: 2.454

4.  Dynamic kinetic resolution of transient hemiketals: a strategy for the desymmetrisation of prochiral oxetanols.

Authors:  Alexander Sandvoß; Henning Maag; Constantin G Daniliuc; Dieter Schollmeyer; Johannes M Wahl
Journal:  Chem Sci       Date:  2022-05-04       Impact factor: 9.969

5.  A C-H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs.

Authors:  Dustin J Covell; M Christina White
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

6.  Total Synthesis of Cryptocaryol A by Enantioselective Iridium-Catalyzed Alcohol C-H Allylation.

Authors:  Felix Perez; Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-11       Impact factor: 15.336

Review 7.  Bioinspired iterative synthesis of polyketides.

Authors:  Kuan Zheng; Changmin Xie; Ran Hong
Journal:  Front Chem       Date:  2015-05-21       Impact factor: 5.221

8.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

  8 in total

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