Literature DB >> 16048335

Catalytic enantioselective Diels-Alder reaction by self-assembly of the components on a Lewis acid template.

Dale E Ward1, Michael Santos Souweha.   

Abstract

Thermal Diels-Alder reaction of 2,4-hexadienol with methyl acrylate is unselective. By simultaneous coordination of diene and dienophile to a chiral bimetallic Lewis acid catalyst, a LACASA-DA reaction occurs with complete control of regio-, diastereo-, and enantioselectivity to give a single adduct. [reaction: see text]

Entities:  

Year:  2005        PMID: 16048335     DOI: 10.1021/ol051262e

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


  4 in total

1.  Stereoselective Synthesis of the Decahydrofluorene Core of the Hirsutellones.

Authors:  Geoff T Halvorsen; William R Roush
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Design, synthesis, and biological evaluation of truncated superstolide A.

Authors:  Lei Chen; Kausar Begam Riaz Ahmed; Peng Huang; Zhendong Jin
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-13       Impact factor: 15.336

3.  Discoveries from the Abyss: The Abyssomicins and Their Total Synthesis.

Authors:  K C Nicolaou; Scott T Harrison; Jason S Chen
Journal:  Synthesis (Stuttg)       Date:  2009-01-01       Impact factor: 3.157

4.  Enantiodivergent [4+2] Cycloaddition of Dienolates by Polyfunctional Lewis Acid/Zwitterion Catalysis.

Authors:  Vukoslava Miskov-Pajic; Felix Willig; Daniel M Wanner; Wolfgang Frey; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-28       Impact factor: 15.336

  4 in total

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