Method for the preparation of optically active...

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing

Reexamination Certificate

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C568S814000, C502S155000

Reexamination Certificate

active

08044245

ABSTRACT:
Optically active 2-sulfonyloxy-1-phenylethanol derivative of formula (II) can be prepared easily and selectively by the method of the present invention using an asymmetric reduction of an α-sulfonyloxy acetophenone compound with a rhodium catalyst having petamethylcyclopentadienyl group and a hydrogen donor, and the compound of formula (II) obtained in the inventive method exhibits a higher e.e. (enantiomer excess) value than that of the products in the conventional methods.

REFERENCES:
Peach, P., et al., “Asymmetric transfer hydrogenation of α,β-unsaturated, α-tosyloxy and α-substituted ketones,” Tetrahedron, 62, 2006, 1864-1876.
Cross, D.J., et al., “Rhodium versus ruthenium: contrasting behaviour in the asymmetric transfer hydrogenation of α-substituted acetophenones,” Tetrahedron: Asymmetry 12 (2001) 1801-1806.
Cho, B.T., et al., “Convenient synthesis of optically active 1,2-diol monosulfonates and terminal epoxides via oxazaborolidine-catalyzed asymmetric borane reduction of α-sulfonyloxy ketones,” J. Chem. Soc., Perkin Trans. 1, 2001, 1204-1211.
Kim, D.J., et al., “A New Approach to the Synthesis of Optically Active Norephedrine, Norpseudoephedrine and Cathinone via Double Asymmetric Induction,” Bull. Korean Chem. Soc., 24:11, 2003. pp. 1641-1648.

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