Journal article
Asymmetric syntheses of (2R,3S)-3-hydroxyproline and (2S,3S)-3-hydroxyproline
- Abstract:
- Two synthetic routes have been developed for the asymmetric syntheses of (2R,3S)- and (2S,3S)-3-hydroxyproline. The key synthetic step in each of these strategies is the conversion of protected α,δ-dihydroxy-β-amino esters (either 2,3-anti- or 2,3-syn-configured) into β,δ-dihydroxy-α-amino esters (protected forms thereof), via the intermediacy of the corresponding aziridinium ions. The products of these stereospecific rearrangements were then cyclized and deprotected to afford (2R,3S)-3-hydroxyproline and (2S,3S)-3-hydroxyproline as single diastereoisomers (>99:1 dr) in >26% overall yield.
- Publication status:
- Published
- Peer review status:
- Peer reviewed
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Access Document
- Files:
-
-
(Preview, Accepted manuscript, pdf, 824.1KB, Terms of use)
-
- Publisher copy:
- 10.1021/acs.orglett.8b01736
Authors
- Publisher:
- ACS Publications
- Journal:
- Organic Letters More from this journal
- Volume:
- 20
- Issue:
- 13
- Pages:
- 4135-4139
- Publication date:
- 2018-06-26
- Acceptance date:
- 2018-06-26
- DOI:
- EISSN:
-
1523-7052
- ISSN:
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1523-7060
- Pmid:
-
29943568
- Language:
-
English
- Pubs id:
-
pubs:859944
- UUID:
-
uuid:a149c217-8955-42b0-9e5a-ff8a000cb6e6
- Local pid:
-
pubs:859944
- Source identifiers:
-
859944
- Deposit date:
-
2018-07-02
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2018
- Notes:
- © 2018 American Chemical Society. This is the accepted manuscript version of the article. The final version is available online from American Chemical Society at: https://doi.org/10.1021/acs.orglett.8b01736
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