Further application of an N-Ar axially chiral mimetic-type ligand: Asymmetric Grignard cross-coupling reaction

A novel chiral ligand mimicking N-Ar axial chirality, (S)-N-[2-(diphenylphosphanyl)naphthalen-1-yl]-2-(piperidinylmethyl)piperidine, was found to exhibit good enantio selectivity (up to 80% ee) in the asymmetric cross-coupling reaction of 1-phenylethylmagnesium chloride with beta-bromostyrene deriva...

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Bibliographic Details
Published inSynlett no. 13; pp. 2047 - 2051
Main Authors Horibe, H, Kazuta, K, Kotoku, M, Kondo, K, Okuno, H, Murakami, Y, Aoyama, T
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENTS
TRANSITION-METAL COMPLEXES
FULLERENE SUBSTITUENT
NICKEL-CATALYST
optically active ligand
ALLYLIC ALKYLATION
PALLADIUM COMPLEX
N-Ar axis
1-PHENYLETHYLMAGNESIUM CHLORIDE
chiral mimetics
asymmetric Kumada-Corriu reaction
PHOSPHINE-LIGANDS
TERTIARY PHOSPHINES
Grignard cross-coupling
BEARING
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Summary:A novel chiral ligand mimicking N-Ar axial chirality, (S)-N-[2-(diphenylphosphanyl)naphthalen-1-yl]-2-(piperidinylmethyl)piperidine, was found to exhibit good enantio selectivity (up to 80% ee) in the asymmetric cross-coupling reaction of 1-phenylethylmagnesium chloride with beta-bromostyrene derivatives. Additionally, this type ligand is appealing, because it allows the synthesis of a wide variety of analogues.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-41485