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Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3‐Chloroindolenines
Author(s) -
Saya Jordy M.,
van Wordragen Ellen D. H.,
Orru Romano V. A.,
Ruijter Eelco
Publication year - 2019
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.201801745
Subject(s) - chemistry , indole test , in situ , combinatorial chemistry , natural product , reaction conditions , organic chemistry , catalysis
C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ‐generated 3‐chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3‐substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.