Literature DB >> 20617821

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

Jeffrey D Butler1, Wayne E Conrad, Michael W Lodewyk, James C Fettinger, Dean J Tantillo, Mark J Kurth.   

Abstract

A diastereoselective organocatalytic aldol/oxa-Michael reaction has been developed to efficiently deliver medicinally relevant 2,3-ring-substituted chromanones. Development of this synthetic strategy revealed an unexpected kinetic anti-Saytzeff elimination; an origin for the observed selectivity is suggested on the basis of the results of quantum chemical calculations. This unusual kinetic selectivity necessitated an isomerization protocol that in turn led to the discovery of an intriguing Pd-mediated isomerization/intramolecular Friedel-Crafts-type alkylation.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20617821      PMCID： PMC3164863          DOI： 10.1021/ol101221c

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


  11 in total

1.  Catalytic enantioselective synthesis of flavanones and chromanones.

Authors:  Margaret M Biddle; Michael Lin; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2007-03-10       Impact factor: 15.419

Review 2.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

3.  The physical origin of Saytzeff's rule.

Authors:  Benoit Braida; Vinca Prana; Philippe C Hiberty
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Catalytic enantioselective Conia-ene reaction.

Authors:  Britton K Corkey; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

5.  Hydantoin bioisosteres. In vivo active spiro hydroxy acetic acid aldose reductase inhibitors.

Authors:  C A Lipinski; C E Aldinger; T A Beyer; J Bordner; D F Burdi; D L Bussolotti; P B Inskeep; T W Siegel
Journal:  J Med Chem       Date:  1992-06-12       Impact factor: 7.446

6.  Efficient and selective Al-catalyzed alcohol oxidation via Oppenauer chemistry.

Authors:  Christopher R Graves; Bi-Shun Zeng; SonBinh T Nguyen
Journal:  J Am Chem Soc       Date:  2006-10-04       Impact factor: 15.419

7.  Asymmetric catalysis: resin-bound hydroxyprolylthreonine derivatives in enamine-mediated reactions.

Authors:  Richard D Carpenter; James C Fettinger; Kit S Lam; Mark J Kurth
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

8.  Design and synthesis of propeller-shaped dispiroisoxazolinopiperidinochromanones.

Authors:  Richard D Carpenter; Patrick B DeBerdt; Jason B Holden; Kristin A Milinkevich; Taewoo Min; Dan Willenbring; James C Fettinger; Dean J Tantillo; Mark J Kurth
Journal:  J Comb Chem       Date:  2008-01-31

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

Authors:  Hiroshi Takikawa; Keisuke Suzuki
Journal:  Org Lett       Date:  2007-06-09       Impact factor: 6.005

10.  Stereoselective synthesis of 4-dehydroxydiversonol employing enantioselective palladium-catalysed domino reactions.

Authors:  Lutz F Tietze; Dirk A Spiegl; Florian Stecker; Julia Major; Christian Raith; Christian Große
Journal:  Chemistry       Date:  2008       Impact factor: 5.020
View more
  1 in total

1.  Substituent Effects on NMR Spectroscopy of 2,2-Dimethylchroman-4-one Derivatives: Experimental and Theoretical Studies.

Authors:  Daniela Iguchi; Davide Ravelli; Rosa Erra-Balsells; Sergio M Bonesi
Journal:  Molecules       Date:  2020-04-28       Impact factor: 4.411
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.