Enantioselective Narasaka-Heck cyclizations: synthesis of tetrasubstituted nitrogen-bearing stereocenters

The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5- cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-be...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2017-03, Vol.8 (3), p.1981-1985
Main Authors: Race, Nicholas J, Faulkner, Adele, Fumagalli, Gabriele, Yamauchi, Takayuki, Scott, James S, Rydén-Landergren, Marie, Sparkes, Hazel A, Bower, John F
Format: Article
Language:English
Subjects:
Alkenes
Bonding
Esters
Insertion
Oximes
Synthesis
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Summary:The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5- cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90 : 10 to 95 : 5 e.r. These processes are rare examples of reactions that proceed enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc04466b