Details
| Original language | English |
|---|---|
| Pages (from-to) | 8210-8214 |
| Number of pages | 5 |
| Journal | Organic letters |
| Volume | 25 |
| Issue number | 46 |
| Early online date | 9 Nov 2023 |
| Publication status | Published - 24 Nov 2023 |
Abstract
Homoallylic alcohols possessing chiral β-centers are considered highly valuable in the synthesis of polyketide-based natural products. Therefore, there is a significant demand for new methods that allow for their stereoselective access. In pursuit of this objective, we have successfully combined our substrate-controlled protocol of Hoppe-Matteson-Aggarwal chemistry with iterative 1,2-metallate rearrangements. Notably, this approach has proven effective in introducing not only primary alcohols but also other functional groups such as alkynes and protected amines.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic letters, Vol. 25, No. 46, 24.11.2023, p. 8210-8214.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Stereoselective Construction of β-chiral Homoallyl Functionalities by Substrate- and Reagent-Controlled Iterative 1,2-Metallate Rearrangements
AU - Kalesse, Markus
AU - Linne, Elvira
N1 - Funding information: A generous gift of B2pin2 from Allychem (China) is appreciated. We thank the analytical department of the OCI (Leibniz University Hannover, Germany) for their support. We also thank Dr. D. Lücke (Enamine Germany GmbH) for helpful discussions on the manuscript. Special thanks to T. Heinrich (University of Leipzig, Germany) for designing the TOC graphic.
PY - 2023/11/24
Y1 - 2023/11/24
N2 - Homoallylic alcohols possessing chiral β-centers are considered highly valuable in the synthesis of polyketide-based natural products. Therefore, there is a significant demand for new methods that allow for their stereoselective access. In pursuit of this objective, we have successfully combined our substrate-controlled protocol of Hoppe-Matteson-Aggarwal chemistry with iterative 1,2-metallate rearrangements. Notably, this approach has proven effective in introducing not only primary alcohols but also other functional groups such as alkynes and protected amines.
AB - Homoallylic alcohols possessing chiral β-centers are considered highly valuable in the synthesis of polyketide-based natural products. Therefore, there is a significant demand for new methods that allow for their stereoselective access. In pursuit of this objective, we have successfully combined our substrate-controlled protocol of Hoppe-Matteson-Aggarwal chemistry with iterative 1,2-metallate rearrangements. Notably, this approach has proven effective in introducing not only primary alcohols but also other functional groups such as alkynes and protected amines.
UR - http://www.scopus.com/inward/record.url?scp=85178129433&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.3c02935
DO - 10.1021/acs.orglett.3c02935
M3 - Article
AN - SCOPUS:85178129433
VL - 25
SP - 8210
EP - 8214
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 46
ER -