Catalytic Asymmetric Vinylogous Mannich Reaction of N-(2-Thienyl)sulfonylimines

Both cyclic and acyclic silyl dienol ethers participate efficiently in the asymmetric vinylogous Mannich reaction of N-2-thienylsulfonylimines catalyzed by copper(I) complexes of Fesulphos ligands. This procedure displays wide imine and nucleophile versatility, high enantiocontrol, and complete γ-re...

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Published inOrganic letters Vol. 10; no. 19; pp. 4335 - 4337
Main Authors Salvador González, Alvaro, Gómez Arrayás, Ramón, Rodríguez Rivero, Marta, Carretero, Juan C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.10.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BRONSTED ACID
ALDOL REACTIONS
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Summary:Both cyclic and acyclic silyl dienol ethers participate efficiently in the asymmetric vinylogous Mannich reaction of N-2-thienylsulfonylimines catalyzed by copper(I) complexes of Fesulphos ligands. This procedure displays wide imine and nucleophile versatility, high enantiocontrol, and complete γ-regioselectivity in most cases examined. The mild sulfonamide deprotection allows the resulting products to be readily transformed into optically active δ-lactams or 5-hydroxy-2-piperidone derivatives.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol8019082