Synthesis and Properties of Optically Pure Phenols Derived from (+)-Dehydroabietylamine

Abstract

Enantiomerically pure phenols are readily available in a straightforward sequence starting from (+)-dehydroabietylamine. Detailed synthetic protocols, analytical data and conversion to a monodentate phosphite ligand are presented.

Key words

phenols - chiral pool - amines - natural products - dehydroabietane

References

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4

Commercially available (+)-dehydroabietylamine contains about 60% of 4 contaminated with the remainings of other amines and hydrocarbons.

5

All procedures were reproduced in scales of up to 25 g.

14

Nitro compound 12 is not inert towards phosphite derivatives and was therefore not used as precursor for phosphite ligands.

15

Yield corresponds to the content of (+)-dehydroabietylamine in the starting material, which was checked by GC methods.

16

CCDC 624454 and 624455 contain the supplementary crystallographic data for compounds 6 and 9, respectively, of this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; E-mail: [e-mail].