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Selenocystine Peptides Performance in 5‐ endo‐dig Reactions
Author(s) -
Lapcinska Sindija,
Arsenyan Pavel
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901548
Subject(s) - dig , chemistry , electrophile , moiety , selenocysteine , lewis acids and bases , bromide , selenium , phenols , stereochemistry , combinatorial chemistry , organic chemistry , medicinal chemistry , cysteine , catalysis , computer security , computer science , enzyme
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.