Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst

Jochanan Blum; Dmitri Gelman; Zeev Aizenshtat; Sonja Wernik; Herbert Schumann

doi:10.1016/S0040-4039(98)01054-5

Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst

Jochanan Blum^*
, Dmitri Gelman
, Zeev Aizenshtat
, Sonja Wernik
, Herbert Schumann

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

33 Scopus citations

Abstract

Kinetic resolution of the racemic title compound was shown to take place during its methylation with either (Me₂AlOCH₂CH₂OMe)₂ or Me₂Al(CH₂)₃NMe₂ in the presence of an optically active Pd(binap) catalyst, as well as during its alkylation with either (S)-(+)- [Me₂AlOCH₂CH(Me)OCH₂Ph]₂ or (S)-(+)-[Me₂AlOCH₂CH(CH₂CHMe₂)NMe₂]₂ in the presence of an achiral palladium complex. The ee values of the resolved binaphthyl derivatives by the two methods were up to 69 and 12%, respectively. The latter method represents the first application of a stabilized dialkylaluminum complex with a chiral chelating ligand for asymmetric induction.

Original language	English
Pages (from-to)	5611-5614
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(98)01054-5
State	Published - 30 Jul 1998

Keywords

Alkylation
Aluminum compounds
Asymmetric induction
Palladium compounds

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Blum, J., Gelman, D., Aizenshtat, Z., Wernik, S., & Schumann, H. (1998). Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst. Tetrahedron Letters, 39(31), 5611-5614. https://doi.org/10.1016/S0040-4039(98)01054-5

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title = "Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst",

abstract = "Kinetic resolution of the racemic title compound was shown to take place during its methylation with either (Me2AlOCH2CH2OMe)2 or Me2Al(CH2)3NMe2 in the presence of an optically active Pd(binap) catalyst, as well as during its alkylation with either (S)-(+)- [Me2AlOCH2CH(Me)OCH2Ph]2 or (S)-(+)-[Me2AlOCH2CH(CH2CHMe2)NMe2]2 in the presence of an achiral palladium complex. The ee values of the resolved binaphthyl derivatives by the two methods were up to 69 and 12\%, respectively. The latter method represents the first application of a stabilized dialkylaluminum complex with a chiral chelating ligand for asymmetric induction.",

keywords = "Alkylation, Aluminum compounds, Asymmetric induction, Palladium compounds",

author = "Jochanan Blum and Dmitri Gelman and Zeev Aizenshtat and Sonja Wernik and Herbert Schumann",

year = "1998",

month = jul,

day = "30",

doi = "10.1016/S0040-4039(98)01054-5",

language = "אנגלית",

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journal = "Tetrahedron Letters",

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Blum, J, Gelman, D, Aizenshtat, Z, Wernik, S & Schumann, H 1998, 'Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst', Tetrahedron Letters, vol. 39, no. 31, pp. 5611-5614. https://doi.org/10.1016/S0040-4039(98)01054-5

Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst. / Blum, Jochanan; Gelman, Dmitri; Aizenshtat, Zeev et al.
In: Tetrahedron Letters, Vol. 39, No. 31, 30.07.1998, p. 5611-5614.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst

AU - Blum, Jochanan

AU - Gelman, Dmitri

AU - Aizenshtat, Zeev

AU - Wernik, Sonja

AU - Schumann, Herbert

PY - 1998/7/30

Y1 - 1998/7/30

N2 - Kinetic resolution of the racemic title compound was shown to take place during its methylation with either (Me2AlOCH2CH2OMe)2 or Me2Al(CH2)3NMe2 in the presence of an optically active Pd(binap) catalyst, as well as during its alkylation with either (S)-(+)- [Me2AlOCH2CH(Me)OCH2Ph]2 or (S)-(+)-[Me2AlOCH2CH(CH2CHMe2)NMe2]2 in the presence of an achiral palladium complex. The ee values of the resolved binaphthyl derivatives by the two methods were up to 69 and 12%, respectively. The latter method represents the first application of a stabilized dialkylaluminum complex with a chiral chelating ligand for asymmetric induction.

AB - Kinetic resolution of the racemic title compound was shown to take place during its methylation with either (Me2AlOCH2CH2OMe)2 or Me2Al(CH2)3NMe2 in the presence of an optically active Pd(binap) catalyst, as well as during its alkylation with either (S)-(+)- [Me2AlOCH2CH(Me)OCH2Ph]2 or (S)-(+)-[Me2AlOCH2CH(CH2CHMe2)NMe2]2 in the presence of an achiral palladium complex. The ee values of the resolved binaphthyl derivatives by the two methods were up to 69 and 12%, respectively. The latter method represents the first application of a stabilized dialkylaluminum complex with a chiral chelating ligand for asymmetric induction.

KW - Alkylation

KW - Aluminum compounds

KW - Asymmetric induction

KW - Palladium compounds

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SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Blum J, Gelman D, Aizenshtat Z, Wernik S, Schumann H. Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst. Tetrahedron Letters. 1998 Jul 30;39(31):5611-5614. doi: 10.1016/S0040-4039(98)01054-5

Kinetic resolution of racemic 2,2'-bis(trifluoromethanesulfonyloxy)- 1,1'-binaphthalene by chiral dimethylaluminum complexes and an achiral Pd catalyst, as well as by achiral dimethylaluminum reagents in the presence of a chiral Pd catalyst

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