Chiral imines and amines based on 2-hydroxypinan-3-one

The new chiral derivatives of benzylamine and 2 α -hydroxypinan-3-one (1 R ,2 R ,5 R )-3-[(1 S )- α -methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (2), (1 S ,2 S ,3 S ,5 S )-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (3), and (1 R ,2 R ,3 R ,5 R )-3-[(1 S )- α -methylbenz...

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Bibliographic Details
Published in:Chemistry of natural compounds 2011, Vol.46 (6), p.920-923
Main Authors: Gur’eva, Ya. A., Zalevskaya, O. A., Frolova, L. L., Alekseev, I. N., Kuchin, A. V.
Format: Article
Language:English
Subjects:
Amines
Medicine
Organic Chemistry
Organic compounds
Pharmacy
Plant Sciences
Schiff bases
Stereoisomers
Synthesis
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Summary:The new chiral derivatives of benzylamine and 2 α -hydroxypinan-3-one (1 R ,2 R ,5 R )-3-[(1 S )- α -methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (2), (1 S ,2 S ,3 S ,5 S )-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (3), and (1 R ,2 R ,3 R ,5 R )-3-[(1 S )- α -methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (4) were synthesized and characterized. It was shown that reduction of the benzylimines by sodium triacetoxyborohydride formed stereoselectively 3 β -substituted pinanamines.
ISSN:0009-3130
1573-8388
DOI:10.1007/s10600-011-9783-x