Journal article
Squarate desymmetrisation–ozonolysis as an approach to β-substituted-α-ketosuccinates and squalestatin synthesis
- Abstract:
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Silylated tertiary alcohols from 1,2-addition of alkyllithiums to dialkyl squarates undergo alkene ozonolysis to give β-substituted-α-keto-β-(silyloxy)succinates. With 3-(triethylsilyloxy)butyllithium the methodology was applied to the 2,8-dioxabicyclo[3.2.1]octane core of the squalestatins. Enantioselective 1,2-addition to di-tert-butyl squarate using butyllithium or diethylzinc/Ti(iPrO)4 in the presence of chiral ligands (such as bisoxazolines or camphorsulfonamides, respectively) gave the ...
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- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 456.5KB, Terms of use)
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- Publisher copy:
- 10.1016/j.tet.2019.130747
Authors
Bibliographic Details
- Publisher:
- Elsevier
- Journal:
- Tetrahedron More from this journal
- Volume:
- 75
- Issue:
- 50
- Article number:
- 130747
- Publication date:
- 2019-11-05
- Acceptance date:
- 2019-10-24
- DOI:
- EISSN:
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1464-5416
- ISSN:
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0040-4020
Item Description
- Language:
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English
- Keywords:
- Pubs id:
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pubs:1077281
- UUID:
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uuid:da4d3ee3-b2f4-43b1-bb4b-864108faaf13
- Local pid:
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pubs:1077281
- Source identifiers:
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1077281
- Deposit date:
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2019-12-15
Terms of use
- Copyright holder:
- Elsevier Ltd
- Copyright date:
- 2019
- Rights statement:
- © 2019 Elsevier Ltd. All rights reserved.
- Notes:
-
This is the accepted manuscript version of the article. The final version is available from Elsevier at https://doi.org/10.1016/j.tet.2019.130747
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