Kinetic resolution of secondary carbinols by a chiral N,N-4-dimethylaminopyridine derivative containing a 1,1′-binaphthyl unit: Hydrogen bonding affects catalytic activity and enantioselectivity

Kazuki Fujii, Koichi Mitsudo, Hiroki Mandai, Seiji Suga

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8 Citations (Scopus)

Abstract

We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-Alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or DMAP. Hydrogen bonding between tert-Alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.

Original languageEnglish
Pages (from-to)1081-1092
Number of pages12
JournalBulletin of the Chemical Society of Japan
Volume89
Issue number9
DOIs
Publication statusPublished - 2016

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Enantioselectivity
Methanol
Catalyst activity
Hydrogen bonds
Derivatives
Kinetics
Alcohols
Methyl Ethers
Catalysts
Reaction rates
4-N,N-dimethylaminopyridine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-Alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or DMAP. Hydrogen bonding between tert-Alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.",
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T1 - Kinetic resolution of secondary carbinols by a chiral N,N-4-dimethylaminopyridine derivative containing a 1,1′-binaphthyl unit

T2 - Hydrogen bonding affects catalytic activity and enantioselectivity

AU - Fujii, Kazuki

AU - Mitsudo, Koichi

AU - Mandai, Hiroki

AU - Suga, Seiji

PY - 2016

Y1 - 2016

N2 - We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-Alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or DMAP. Hydrogen bonding between tert-Alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.

AB - We developed an acylative kinetic resolution of secondary carbinols using a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1d with tert-Alcohol substituents. The reaction proceeded with a wide range of carbinols with moderate to high selectivity (s) (up to s = 79.5). Kinetic studies revealed that catalyst 1d was more catalytically active than the corresponding bis-methyl ether 1d′ or DMAP. Hydrogen bonding between tert-Alcohols of the catalyst and secondary carbinols was responsible for the enhanced reaction rate and high enantioselectivity.

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