Palladium-catalyzed intramolecular allylic alkylation of α-sulfinyl carbanions: a new asymmetric route to enantiopure γ-lactams

A simple and efficient protocol for the intramolecular palladium-catalyzed allylic alkylation of α-sulfinyl carbanions is reported. The use of unsaturated amides bearing a sulfinyl group of defined absolute configuration in concomitance with enantiopure BINAP as the ligand in a biphasic medium provi...

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Bibliographic Details
Published inTetrahedron letters Vol. 51; no. 11; pp. 1459 - 1461
Main Authors Vogel, Sophie, Bantreil, Xavier, Maitro, Guillaume, Prestat, Guillaume, Madec, David, Poli, Giovanni
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 17.03.2010
Elsevier
Subjects
Allylic alkylation
Catalysis
Chemistry
Chemistry, Organic
Enantioselective
Lactam
Palladium
Physical Sciences
Science & Technology
Sulfoxide
Sulfoxide
Allylic alkylation
Palladium
Enantioselective
Catalysis
Lactam
OXIDATION
LIGANDS
SULFIDES
CARBONYL-COMPOUNDS
SULFONES
ALLYLATIONS
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Summary:A simple and efficient protocol for the intramolecular palladium-catalyzed allylic alkylation of α-sulfinyl carbanions is reported. The use of unsaturated amides bearing a sulfinyl group of defined absolute configuration in concomitance with enantiopure BINAP as the ligand in a biphasic medium provided good diastereoselectivities. Asymmetric intramolecular palladium-catalyzed allylic alkylation allowing access to disubstituted sulfinyl γ-lactams is described. The use of unsaturated amides bearing a sulfinyl group of defined absolute configuration together with enantiopure BINAP as the ligand in a biphasic medium provided good diastereoselectivities with clear solvent effect.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.01.012