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© 2014 The Japan Institute of Heterocyclic Chemistry. Treatment of 10,11-dimethoxyaporphine with chromium hexacarbonyl was found to give two diastereoisomeric products on regioselective co-ordination of the chromium tricarbonyl fragment to the A ring. For one of the diastereoisomeric complexes, alkylation was found to proceed with high regio- and diastereoselectivity at C(4), whereas regio- and diastereoselective alkylation was observed at C(6a) for the other diastereoisomer. In the case of the C(4)- and C(6a)-methylated products, these substrates were decomplexed in high yield to give the corresponding enantiopure, C(4)- and C(6a)-methyl substituted aporphines.

Original publication

DOI

10.3987/COM-13-S(S)39

Type

Journal article

Journal

Heterocycles

Publication Date

01/01/2014

Volume

88

Pages

765 - 777