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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-hydro...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1021/acs.orglett.8b01736

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More by this author
Institution:
University of Oxford
Division:
Maths, Physical and Life Sciences
Department:
Chemistry; Organic Chemistry
Role:
Author
ORCID:
0000-0003-3181-8748
More by this author
Institution:
University of Oxford
Division:
Maths, Physical and Life Sciences
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
Maths, Physical and Life Sciences
Department:
Chemistry; Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
Maths, Physical and Life Sciences
Department:
Chemistry; Organic Chemistry
Role:
Author
Publisher:
ACS Publications Publisher's website
Journal:
Organic Letters Journal website
Volume:
20
Issue:
13
Pages:
4135-4139
Publication date:
2018-06-26
Acceptance date:
2018-06-26
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pubs id:
pubs:859944
URN:
uri:a149c217-8955-42b0-9e5a-ff8a000cb6e6
UUID:
uuid:a149c217-8955-42b0-9e5a-ff8a000cb6e6
Local pid:
pubs:859944
Language:
English

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