Solvent-dependent divergent functions of Sc(OTf)3 in stereoselective epoxide-opening spiroketalizations Journal Article

   


Authors: Sharma, I.; Wurst, J. M.; Tan, D. S.
Article Title: Solvent-dependent divergent functions of Sc(OTf)3 in stereoselective epoxide-opening spiroketalizations
Abstract: A stereocontrolled synthesis of benzannulated spiroketals has been developed using solvent-dependent Sc(OTf)3-mediated spirocyclizations of exo-glycal epoxides having alcohol side chains. In THF, the reaction proceeds via Lewis acid catalysis under kinetic control with inversion of configuration at the anomeric carbon. In contrast, in CH2Cl 2, Brønsted acid catalysis under thermodynamic control leads to retention of configuration. The reactions accommodate a variety of aryl substituents and ring sizes and provide stereochemically diverse spiroketals. © 2014 American Chemical Society.
Journal Title: Organic Letters
Volume: 16
Issue: 9
ISSN: 1523-7060
Publisher: American Chemical Society  
Date Published: 2014-05-02
Start Page: 2474
End Page: 2477
Language: English
DOI: 10.1021/ol500853q
PROVIDER: scopus
PMCID: PMC4018158
PUBMED: 24742081
DOI/URL:

http://www.scopus.com/inward/record.url?eid=2-s2.0-84899889933&partnerID=40&md5=6fb56a70dc111226372621d8d6b5b175
Notes: Org. Lett. -- Export Date: 2 June 2014 -- CODEN: ORLEF -- Source: Scopus
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MSK Authors
  1. Derek S Tan
    91 Tan
  2. Indrajeet Sharma
    5 Sharma
  3. Jacqueline M Wurst
    5 Wurst
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