Toward Enantiomerically Pure β‑Seleno-α-amino Acids via Stereoselective Se-Michael Additions to Chiral Dehydroalanines

The first totally chemo- and diastereoselective 1,4-conjugate additions of Se-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. The methodology is simple and does not require any catalyst, providing exceptional yields at room temperature, and involves the treatment of the corresp...

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Published inOrganic letters Vol. 23; no. 6; pp. 1955 - 1959
Main Authors Oroz, Paula, Navo, Claudio D, Avenoza, Alberto, Busto, Jesús H, Corzana, Francisco, Jiménez-Osés, Gonzalo, Peregrina, Jesús M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:The first totally chemo- and diastereoselective 1,4-conjugate additions of Se-nucleophiles to a chiral bicyclic dehydroalanine (Dha) are described. The methodology is simple and does not require any catalyst, providing exceptional yields at room temperature, and involves the treatment of the corresponding diselenide compound with NaBH4 in the presence of the Dha. These Se-Michael additions provide an excellent channel for the synthesis of enantiomerically pure selenocysteine (Sec) derivatives, which pose high potential for chemical biology applications.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03832