Iron-Catalyzed Enantioselective Intramolecular Inverse Electron-Demand Hetero Diels–Alder Reactions: An Access to Bicyclic Dihydropyran Derivatives | Zendy

Jimmy Lauberteaux | Zendy; Aurélien Lebrun | Zendy; Arie van der Lee | Zendy; Marc Mauduit | Zendy; Renata Marcia de Figueiredo | Zendy; JeanMarc Campagne | Zendy

Open Access

Iron-Catalyzed Enantioselective Intramolecular Inverse Electron-Demand Hetero Diels–Alder Reactions: An Access to Bicyclic Dihydropyran Derivatives

Author(s) -

Jimmy Lauberteaux,

Aurélien Lebrun,

Arie van der Lee,

Marc Mauduit,

Renata Marcia de Figueiredo,

JeanMarc Campagne

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03752

Subject(s) - dihydropyran , chemistry , enantioselective synthesis , intramolecular force , bicyclic molecule , moiety , catalysis , imidazole , combinatorial chemistry , stereochemistry , organic chemistry

A highly enantioselective iron-catalyzed Intramolecular Inverse Electron-Demand Hetero Diels-Alder (IIEDHDA) reaction is reported. By using a chiral semicorrin ligand in the presence of 2,6-lutidine, good isolated yields and excellent enantioselectivities were observed (up to 96% ee). Thanks to the versatile postfunctionalization of the acyl-imidazole moiety, this methodology represents a unique example of the straightforward construction of highly valuable enantioenriched bicyclic dihydropyran derivatives.

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