Asymmetric synthesis of (R)- and (S)-arylethanolamines from imin

Details Asymmetric synthesis of (R)- and (S)-arylethanolamines from imin Asymmetric synthesis of (R)- and (S)-arylethanolamines from imin

1994-04-22

1995-08-15

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564357, 564361, 564363, 564365, 564415, 564489, C07C21300

Patent

active

054421187

ABSTRACT:
A method for the enantioselective reduction of an .alpha.-iminoketone to an .alpha.-aminoalcohol is disclosed. The method utilizes a borane reducing agent as the reducing agent and a chiral 1,3,2-oxazaborole as the catalyst. The method is applied to the synthesis of R-albuterol from methyl 5-acetylsalicylate in high yield and high optical purity.

REFERENCES:
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patent: 5283359 (1994-02-01), Tann et al.
Cho et al, J. Chem. Soc., Perkin Trans. I, (1990) pp. 3200-3201.
Mathre et al. "A Practical Process for the Preparation of Tetrahydro-1-methyl-3,3-diphenyl-1 . . . " J. Org. Chem. 58, 2880-2888 (1993).
Cho et al."Enantioselective Synthesis of Optically Active .beta.-Aminoalcohols via Asymmetric Reduction" Tetrahedron: Asymmetry 3, 341-342 (1992).
Alcaide et al., "Stereochemistry of Imino-group Reduction. Part 6. Stereochemistry of Reduction of 1,2-Imino Ketones . . . " J. Chem Soc. P. II,, 99-103 (1986).
Alcaide et al. "Reduction of N-Substituted 1-Acetyl- and 1-Benzoyl-ethanimines" J.l Chem. Research, 98-99 (1988).

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