An N–Ar axially chiral mimetic. A new approach to ligand design for asymmetric catalysis

A new-type chiral ligand, ( S)- N-[2-(diphenylphosphino)naphthyl]-2-(pyrrolidinylmethyl)piperidine mimicking N–Ar axial chirality, has been developed. This chiral ligand was found to exhibit 99% ee with the use of ( E)-1,3-diphenyl-2-propenyl acetate as the standard substrate, and achieved slightly...

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Bibliographic Details
Published inTetrahedron Vol. 58; no. 26; pp. 5209 - 5214
Main Authors Kondo, Kazuhiro, Kazuta, Kumiko, Fujita, Hiroko, Sakamoto, Yohko, Murakami, Yasuoki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.06.2002
Elsevier
Subjects
asymmetric catalyst
Chemistry
Chemistry, Organic
chiral mimetic
N–Ar axial chirality
P,N-ligand
palladium-catalyzed allylic substitution
Physical Sciences
Science & Technology
asymmetric catalyst
N–Ar axial chirality
chiral mimetic
palladium-catalyzed allylic substitution
P,N-ligand
palladium-catalyzed allytic substitution
COMPLEXES
ALLYLATION
ALLYLIC ALKYLATION
AMINOPHOSPHINES
N-Ar axial chirality
NUCLEOPHILIC AROMATIC-SUBSTITUTION
ACYLATION REAGENTS
PHOSPHINO
ORGANOSULFUR
ACYL-GROUPS
RACEMIZATION
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Summary:A new-type chiral ligand, ( S)- N-[2-(diphenylphosphino)naphthyl]-2-(pyrrolidinylmethyl)piperidine mimicking N–Ar axial chirality, has been developed. This chiral ligand was found to exhibit 99% ee with the use of ( E)-1,3-diphenyl-2-propenyl acetate as the standard substrate, and achieved slightly better results than the Pfaltz and Trost ligands with the use of ( E)-1-phenyl-3-trimethylsilyl-2-propenyl acetate as the substrate, in the palladium-catalyzed asymmetric allylic substitution. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00507-0