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Derailed Ohira‐Bestmann Reaction of γ , δ ‐Unsaturated Aldehydes for the Stereoselective Synthesis of Cyclopenta[ c ]pyrazoles
Author(s) -
Sandmeier Tobias,
Sievertsen Niels,
Carreira Erick M.
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000058
Subject(s) - chemistry , pyrazole , stereoselectivity , diastereomer , intramolecular force , cycloaddition , imine , domino , organic chemistry , combinatorial chemistry , stereochemistry , catalysis
The synthesis of cyclopenta[ c ]pyrazoles from γ , δ ‐unsaturated aldehydes by a domino sequence involving one‐carbon homologation and intramolecular azomethine imine 1,3‐dipolar cycloaddition is disclosed. The fused pyrazoles bearing aromatic and aliphatic substituents are obtained in good yields and excellent diastereomeric purity. Additionally, the synthetic utility of the pyrazole products generated by this method has been highlighted in a series of functionalization reactions. The method presented opens strategic opportunities for the synthesis of pyrazole‐containing biologically active compounds.