
TY  - JOUR
A1  - Castonguay, A 
A1  - Berger, Y 
T1  - (S)-(&#8211;)-Proline Catalysed Alkylation of 1,3-Dihydroxyanthraquinone with Phenylacetaldehyde
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1979
VL  - 32
IS  - 12
SP  - 2681
EP  - 2688
KW  - 
UR  - https://doi.org/10.1071/CH9792681 
N2  - In the presence of the amino acid (S)-(-)-proline, 1,3-dihydroxyanthraquinone (1) is alkylated by phenylacetaldehyde to give an anomeric mixture of lactols (2). The lactols are oxidized to the corresponding lactone (3) by manganese dioxide or chromic acid. Treatment of (2) with p-toluenesulfonic acid yields the expected enol ether (4) along with the substitution product (5). Mass spectrometry fragmentation, high-resolution 1H N.M.R. and 13C n.m.r, studies of these compounds are discussed. 
ER  -

