Literature DB >> 17559218

Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: synthesis of (+)-sappanone B.

Hiroshi Takikawa1, Keisuke Suzuki.   

Abstract

Asymmetric synthesis of (+)-sappanone B (1), a natural product with a 3-hydroxy chromanone structure, was achieved via enantioselective benzoin cyclization by using a modified Rovis catalyst and triethylamine. This catalyst enabled the successful benzoin cyclization of readily enolizable keto-aldehydes.

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Year:  2007        PMID: 17559218     DOI: 10.1021/ol070929p

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


  16 in total

Review 1.  Carbene catalysts.

Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

2.  Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

3.  Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions and kinetic resolution of resultant alpha-silyloxyketones.

Authors:  James C Tarr; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

4.  Synthesis of substituted chromanones: an organocatalytic aldol/oxa-Michael reaction.

Authors:  Jeffrey D Butler; Wayne E Conrad; Michael W Lodewyk; James C Fettinger; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2010-08-06       Impact factor: 6.005

5.  Catalytic enantioselective total syntheses of bakkenolides I, J, and S: application of a carbene-catalyzed desymmetrization.

Authors:  Eric M Phillips; John M Roberts; Karl A Scheidt
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

6.  N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of alpha-protio and alpha-deuterio alpha-chloro and alpha-fluoro carboxylic acids.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

Review 7.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336

8.  Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions.

Authors:  James C Tarr; Jeffrey S Johnson
Journal:  Org Lett       Date:  2009-09-03       Impact factor: 6.005

9.  A Concise Enantioselective Synthesis and Cytotoxic Evaluation of the Anticancer Rotenoid Deguelin Enabled by a Tandem Knoevenagel/Conjugate Addition/Decarboxylation Sequence.

Authors:  Rebecca L Farmer; Karl A Scheidt
Journal:  Chem Sci       Date:  2013-08       Impact factor: 9.825

10.  Asymmetric synthesis of functionalized cyclopentanones via a multicatalytic secondary amine/N-heterocyclic carbene catalyzed cascade sequence.

Authors:  Stephen P Lathrop; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

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