Journal article
HFIP solvent enables alcohols to act as alkylating agents in stereoselective heterocyclization
- Abstract:
- A new method for the stereoselective synthesis of highly functionalized oxygen heterocycles using allyl or benzyl alcohols as alkylating agents is presented. The process is efficient and atom economic, generating water as the only stoichiometric byproduct. Substoichiometric amounts of Ti(OiPr)4 in HFIP solvent are key to this reactivity, and the method tolerates a broad substitution pattern on both the alcohol initiator and homoallylic alcohol substrate. Preliminary mechanistic studies reveal in situ formation of a titanium complex with HFIP which may initiate the cyclization reaction. Further stereoselective functionalization of the products allows access to a diverse range of interesting heterocyclic structures.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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- Files:
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(Preview, Accepted manuscript, pdf, 792.1KB, Terms of use)
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(Preview, Not applicable (or unknown), pdf, 3.0MB, Terms of use)
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(Preview, Not applicable (or unknown), pdf, 19.7MB, Terms of use)
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- Publisher copy:
- 10.1021/jacs.9b02198
Authors
- Publisher:
- American Chemical Society
- Journal:
- Journal of the American Chemical Society More from this journal
- Volume:
- 141
- Issue:
- 16
- Pages:
- 6489-6493
- Publication date:
- 2019-04-12
- Acceptance date:
- 2019-04-09
- DOI:
- EISSN:
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1520-5126
- ISSN:
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0002-7863
- Language:
-
English
- Keywords:
- Pubs id:
-
pubs:987798
- UUID:
-
uuid:4f884062-3f54-4ee3-ae1b-123fbbce17bb
- Local pid:
-
pubs:987798
- Source identifiers:
-
987798
- Deposit date:
-
2019-04-10
- ARK identifier:
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2019
- Rights statement:
- Copyright © 2019 American Chemical Society
- Notes:
- This is the accepted manuscript version of the article. The final version is available online from https://doi.org/10.1021/jacs.9b02198 and supporting information for the paper is available from the American Chemical Society at: https://pubs.acs.org/doi/suppl/10.1021/jacs.9b02198
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