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Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution.
Enantiomer. 1997; 2(3-4):203-13.E

Abstract

Novel chiral aminophosphines, N,N-disubstituted diphenyl(1-amino-2-naphthyl)phosphines 4 were synthesized via nucleophilic aromatic substitution reaction on 1-methoxy-2-(diphenylphosphinoyl)naphthalene (1) by chiral lithium amides 2, followed by reduction of the phosphinoyl function. The new ligands were tested for their efficiency in the palladium-catalyzed allylic substitution of dimethyl malonate with 1,3-diphenyl-2-propenyl acetate and high asymmetric inductions up to 80%ee were observed.

Authors+Show Affiliations

Hattori T
Department of Biochemistry and Engineering, Faculty of Engineering, Tohoku University, Sendai, Japan.
Komuro Y
No affiliation info available
Hayashizaka N
No affiliation info available
Takahashi H
No affiliation info available
Miyano S
No affiliation info available

MeSH

Allyl CompoundsBenzene DerivativesCatalysisMagnetic Resonance SpectroscopyPalladiumPhosphinesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

9676268

Citation

Hattori, T, et al. "Synthesis of Chiral Aminophosphines Via Nucleophilic Aromatic Substitution and Their Application to Palladium-catalyzed Enantioselective Allylic Substitution." Enantiomer, vol. 2, no. 3-4, 1997, pp. 203-13.
Hattori T, Komuro Y, Hayashizaka N, et al. Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution. Enantiomer. 1997;2(3-4):203-13.
Hattori, T., Komuro, Y., Hayashizaka, N., Takahashi, H., & Miyano, S. (1997). Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution. Enantiomer, 2(3-4), 203-13.
Hattori T, et al. Synthesis of Chiral Aminophosphines Via Nucleophilic Aromatic Substitution and Their Application to Palladium-catalyzed Enantioselective Allylic Substitution. Enantiomer. 1997;2(3-4):203-13. PubMed PMID: 9676268.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of chiral aminophosphines via nucleophilic aromatic substitution and their application to palladium-catalyzed enantioselective allylic substitution. AU - Hattori,T, AU - Komuro,Y, AU - Hayashizaka,N, AU - Takahashi,H, AU - Miyano,S, PY - 1997/1/1/pubmed PY - 1998/7/24/medline PY - 1997/1/1/entrez SP - 203 EP - 13 JF - Enantiomer JO - Enantiomer VL - 2 IS - 3-4 N2 - Novel chiral aminophosphines, N,N-disubstituted diphenyl(1-amino-2-naphthyl)phosphines 4 were synthesized via nucleophilic aromatic substitution reaction on 1-methoxy-2-(diphenylphosphinoyl)naphthalene (1) by chiral lithium amides 2, followed by reduction of the phosphinoyl function. The new ligands were tested for their efficiency in the palladium-catalyzed allylic substitution of dimethyl malonate with 1,3-diphenyl-2-propenyl acetate and high asymmetric inductions up to 80%ee were observed. SN - 1024-2430 UR - https://www.unboundmedicine.com/medline/citation/9676268/Synthesis_of_chiral_aminophosphines_via_nucleophilic_aromatic_substitution_and_their_application_to_palladium_catalyzed_enantioselective_allylic_substitution_ DB - PRIME DP - Unbound Medicine ER -