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Brønsted Acid‐Catalyzed [3+2] Cyclodimerization of 3‐Alkyl‐ 2‐vinylindoles Leading to the Diastereoselective Construction of a Pyrroloindole Framework
Author(s) -
Yin Lei,
Wang Yang,
Sun Meng,
Shi Feng
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201501116
Subject(s) - chemistry , alkyl , moiety , brønsted–lowry acid–base theory , catalysis , yield (engineering) , indole test , medicinal chemistry , carbon fibers , stereochemistry , organic chemistry , materials science , composite number , metallurgy , composite material
A Brønsted acid‐catalyzed [3+2] cyclodimerization of 3‐alkyl‐2‐vinylindoles has been established, which led to the diastereoselective construction of pyrroloindole frameworks in high yields (up to 98% yield, all >95:5 dr ). This reaction not only represents the first application of 3‐alkyl‐2‐vinylindoles as nitrogen‐carbon‐carbon (NCC) building blocks, but also reveals a new [3+2] cyclodimerization of 2‐vinylindoles. Control experiments demonstrated that both the free NH group and the C‐3 alkyl group in the indole moiety play a crucial role in performing the [3+2] cyclodimerization. A preliminary attempt also demonstrated the feasibility of performing heterodimerization.