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Chiral phase transfer catalysts (Maruoka catalysts) for organic synthesis
(R,R)-3,5-Bistrifluoromethylphenyl-NAS Bromide
(R,R)-3,4,5-Trifluorophenyl-NAS Bromide

Aqueous quaternary ammonium salts become also soluble in organic solvents with increased lipid solubility accompanying extension of the alkyl chain. During the development of phase transfer catalysts utilizing this property, Professor Maruoka, Kyoto University, devised a novel chiral phase transfer catalyst recently. This is spiro-type chiral ammonium salt with two binaphthyl rings allowing easy molecular designing.

With this (R,R)-3,5-bistrifluoromethylphenyl-NAS bromide, β-hydroxy-α-amino acid derivatives, which are important chiral units in physiological active peptides, are obtained at a high yield by the aldol reaction between a glycine derivative and aldehyde.
Furthermore, it has been found that erythro isomer, which is the main product, is obtained with high enantioselectivity.1)

(R,R)-3,4,5-trifluorophenyl-NAS bromide exhibits high catalyst activity and enantioselectivity in asymmetric alkylation reaction of α-amino acid derivatives.2)

(R,R)-3,5-Bistrifluoromethylphenyl-NAS Bromide
C60H36BrF12N = 1078.82
(R,R)-3,4,5-Trifluorophenyl-NAS Bromide
C56H34NF6Br = 914.77 [287384-12-7]

  1. [Reaction]
    Direct asymmetric aldol reaction to β-hydroxy-α-amino acid derivative

  2. [Reaction]
    Asymmetric alkylation reaction of α-amino acid derivatives

  3. References

  4. Product List

1. Direct asymmetric aldol reaction of β-hydroxy-α-amino acid derivative Ref.1)

2. Asymmetric alkylation reaction of α-amino acid derivatives Ref. 2)

3. References

  1. T. Ooi, M. Taniguchi, M. Kameda, K. Maruoka: " Direct Asymmetric Aldol Reactions of Glycine Schiff Base with Aldehydes Catalyzed by Chiral Quaternary Ammonium Salts", Angew. Chem. Int. Ed., 41, 4542-44 (2002).

  2. T. Ooi, M. Kameda, H. Tannai, K. Maruoka: "Facile synthesis of L-Dopa tert-butyl ester by catalytic enantioselective phase-transfer alkylation", Tetrahedron Lett.,41, 8339-42 (2000).
Angewandte Chemie

Tetrahedron Letters
4. Product List

Product Name Grade Pkg. Size Wako Catalog No.
(R,R)-3,5-Bistrifluoromethylphenyl-NAS Bromide
(Maruoka Catalyst RR-Bistrifluoromethylphenyl Br Form)
for Organic Synthesis 100 mg 029-14921
500 mg 025-14923
(R,R)-3,4,5-Trifluorophenyl-NAS Bromide
(Maruoka Catalyst RR-Trifluorolphenyl Br Form)
for Organic Synthesis 100 mg 201-15921
500 mg 207-15923

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