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The Ruthenium‐Catalyzed Domino Cross Enyne Metathesis/Ring‐Closing Metathesis in the Synthesis of Enantioenriched Nitrogen‐Containing Heterocycles
Author(s) -
Llobat Alberto,
Escorihuela Jorge,
Sedgwick Daniel M.,
Rodenes Miriam,
Román Raquel,
Soloshonok Vadim A.,
Han Jianlin,
MedioSimón Mercedes,
Fustero Santos
Publication year - 2020
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.202000598
Subject(s) - enyne metathesis , chemistry , metathesis , ring closing metathesis , enyne , ruthenium , salt metathesis reaction , combinatorial chemistry , catalysis , conjugated system , organic chemistry , polymerization , polymer
The tetrahydropyridine structure is present in a wide variety of natural and synthetic compounds with interesting pharmacological properties. Therefore, the search for new chemical routes capable of yielding this valuable nitrogen‐containing heterocycle is of utmost interest. Herein, we report the use of the ruthenium‐catalyzed ring‐closing enyne metathesis (RCEYM) and cross enyne metathesis/ring‐closing metathesis (CEYM/RCM) reactions of chiral nitrogen‐containing 1,7‐enynes as an efficient route to synthesize a variety of enantioenriched tetrahydropyridine‐based conjugated 1,3‐dienes. The RCEYM presented wide functional group tolerance and took place in moderate to high yields, with no significant differences when carried out on gram scale. These 1,3‐dienes were suitable for further transformations, such as the Diels–Alder reaction, effectively yielding more complex enantioenriched bicyclic structures.