Journal article
Alcohols as efficient intermolecular initiators for a highly stereoselective polyene cyclisation cascade
- Abstract:
- The use of benzylic and allylic alcohols in HFIP solvent together with Ti(OiPr)4 has been shown to trigger a highly stereoselective polyene cyclisation cascade. Three new carbon-carbon bonds are made during the process and complete stereocontrol of up to five new stereogenic centers is observed. The reaction is efficient, has high functional group tolerance and is atom-economic generating water as a stoichiometric by-product. A new polyene substrate-class is employed, and subsequent mechanistic studies indicate a stereoconvergent mechanism. The products of this reaction can be used to synthesize steroid-analogues in a single step.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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(Preview, Version of record, pdf, 5.5MB, Terms of use)
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- Publisher copy:
- 10.1002/chem.202203732
Authors
- Publisher:
- Wiley
- Journal:
- Chemistry - A European Journal More from this journal
- Volume:
- 29
- Issue:
- 13
- Article number:
- e202203732
- Publication date:
- 2023-01-30
- Acceptance date:
- 2022-12-05
- DOI:
- EISSN:
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1521-3765
- ISSN:
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0947-6539
- Language:
-
English
- Keywords:
- Pubs id:
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1311818
- Local pid:
-
pubs:1311818
- Deposit date:
-
2022-12-07
Terms of use
- Copyright holder:
- Aynetdinova et al.
- Copyright date:
- 2022
- Rights statement:
- © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
- Licence:
- CC Attribution (CC BY)
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