Selenocystine Peptides Performance in 5-endo-dig Reactions
European Journal of Organic Chemistry 2020
Sindija Lapčinska, Pavel Arsenyan

Herein, we present methods for the generation of selenocysteinyl electrophile by weak Lewis acids or oxidants. The electrophilic selenium species were further utilized in 5-endo-dig cyclization reactions with 2-ethynyl phenols, anisoles, and anilines, yielding substituted benzo[b]furans and indoles bearing short selenocysteine-containing peptides. Copper(II) bromide promoted 5-endo-dig cyclization can be successfully applied for protected and unprotected peptides in high yields. Elaborated protocol allows the construction of phenylindeno[1,2-c]chromene moiety in 5-endo-dig/6-endo-dig cascade reactions.


Keywords
5-endo-dig, 6-endo-dig, Diselenide, Peptides, Selenocysteine
DOI
10.1002/ejoc.201901548
Hyperlink
https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201901548

Lapčinska, S., Arsenyan, P. Selenocystine Peptides Performance in 5-endo-dig Reactions. European Journal of Organic Chemistry, 2020, Vol. 2020, No. 7, pp.784-795. ISSN 1434-193X. Available from: doi:10.1002/ejoc.201901548

Publication language
English (en)
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