Enantioselective alkylation of N-diphenylphosphinylimine with dialkylzincs using copolymerized chiral ligands

Takefumi Suzuki, Naoyuki Narisada, Takanori Shibata, Kenso Soai

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Enantioselective alkylation of N-diphenylphosphinylimine with dialkylzincs using monomeric chiral amino alcohols and copolymerized chiral amino alcohols as chiral ligands afforded N-diphenylphosphinylamines with high enantiomeric excess (EE). Among monomeric chiral ligands, N-vinylbenzylephedrine was the most highly enantioselective to afford the corresponding N-diphenylphosphinylamine with 95% EE. Chiral monomeric amino alcohols were copolymerized with styrene in the presence of crosslinking reagents such as divinylbenzene. The enantioselectivities of copolymerized chiral ligands were also high (up to 89% EE). Copolymerized chiral ligand was easily separated from the reaction mixture by filtration and was reused without considerable decrease in the enantioselectivity. Copolymerized chiral ligands prepared using crosslinking reagents with methylene spacers also showed high enantioselectivities, giving N-diphenylphosphinylamine with up to 90% EE. Regarding of the effect of solvent, aromatic hydrocarbons (toluene and benzene) and diethyl ether are appropriate. The effect of a spacer introduced on the nitrogen atom of the amino alcohol was also examined.

Original languageEnglish
Pages (from-to)30-38
Number of pages9
JournalPolymers for Advanced Technologies
Volume10
Issue number1-2
Publication statusPublished - 1999 Jan
Externally publishedYes

Fingerprint

Amino alcohols
Amino Alcohols
Alkylation
Ligands
Enantioselectivity
Cross-Linking Reagents
divinyl benzene
Crosslinking
Aromatic Hydrocarbons
Styrene
Aromatic hydrocarbons
Toluene
Benzene
Ether
Ethers
Nitrogen
Atoms

Keywords

  • Dialkylzinc
  • Enantioselective alkylation
  • Imine
  • Polymer ligand

ASJC Scopus subject areas

  • Polymers and Plastics

Cite this

Enantioselective alkylation of N-diphenylphosphinylimine with dialkylzincs using copolymerized chiral ligands. / Suzuki, Takefumi; Narisada, Naoyuki; Shibata, Takanori; Soai, Kenso.

In: Polymers for Advanced Technologies, Vol. 10, No. 1-2, 01.1999, p. 30-38.

Research output: Contribution to journalArticle

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