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Asymmetric Synthesis of a Fused Tricyclic Hydronaphthofuran Scaffold by Desymmetric [2+2+2] Cycloaddition
Author(s) -
Teng Qi,
Mao Wenxiu,
Chen Dong,
Wang Zhen,
Tung ChenHo,
Xu Zhenghu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201911071
Subject(s) - cycloaddition , stereocenter , enantioselective synthesis , tricyclic , rhodium , chemistry , combinatorial chemistry , atom economy , catalysis , stereochemistry , organic chemistry
A rhodium(I)‐BINAP‐catalyzed highly enantioselective [2+2+2] cycloaddition of enynes with alkynes has been developed. Diverse fused tricyclic hydronaphthofuran scaffolds with three consecutive stereogenic centers were constructed in one step from easily available materials with excellent chemo‐, regio‐, diastereo‐, and enantioselectivity. Notable features of these reactions include 100 % atom economy, very broad scope, and mild reaction conditions.