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Regioselective [3+3] Cyclization of 2‐Indolymethanols with Vinylcyclopropanes via Metal Catalysis
Author(s) -
Zhu ZiQi,
Yu Lei,
Sun Meng,
Mei GuangJian,
Shi Feng
Publication year - 2018
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.201800688
Subject(s) - stereocenter , regioselectivity , chemistry , vicinal , catalysis , iridium , metal , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis
The first [3+3] cyclization of 2‐indolylmethanols with vinylcyclopropanes has been established under iridium catalysis. The reaction regioselectively constructs tetrahydrocarbazole frameworks bearing two vicinal all‐carbon quaternary stereocenters in high yields (up to 99%, up to 20:1 rr). This reaction not only is the first example of a metal‐catalyzed [3+3] cyclization of 2‐indolylmethanols but also is the first one‐step [3+3] cyclization of vinylcyclopropanes. More importantly, this reaction shows reversed regioselectivity compared to other 2‐indolylmethanol‐involved transformations, which will advance the chemistry of 2‐indolylmethanols.