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Enantioselective Synthesis of Sulfur‐Containing Medium‐Ring Heterocycles with Axial Chiralities by Catalytic Intramolecular [2+2+2] Cycloaddition
Author(s) -
Mitake Akihito,
Fusamae Toru,
Kanyiva Kyalo Stephen,
Shibata Takanori
Publication year - 2017
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.201701532
Subject(s) - enantioselective synthesis , chemistry , intramolecular force , cycloaddition , rhodium , ring (chemistry) , catalysis , enantiomer , sulfur , stereochemistry , organic chemistry
The rhodium‐catalyzed enantioselective intramolecular cycloaddition of triynes connected by sulfur‐containing tethers gave tribenzothiepins and a tribenzodithiocin in high yields with good‐to‐excellent enantiomeric excesses. The present protocol generated axial chiralities fused with medium‐ring heterocycles. In particular, this is the first example of the catalytic and highly enantioselective construction of a tribenzodiheterocin skeleton.