Asymmetric Ortholithiation of Amides by Conformationally Mediated Chiral Memory: An Enantioselective Route to Naphtho- and Benzofuranones
- 28 June 2005
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2005 (11) , 1716-1720
- https://doi.org/10.1055/s-2005-871554
Abstract
An enantiomerically pure sulfinyl group ortho to an aromatic amide imposes absolute stereochemistry on the conformation of its Ar-CO axis. Sulfoxide-lithium exchange followed by addition to an aldehyde relays the chirality of the amide axis to the new hydroxyl-bearing stereogenic centre with good stereochemical fidelity. Lactonisation of the hydroxyamide gives naphthofuranones and benzofuranones, including the fungal metabolite isoochracein, but with substrate-dependent stereoselectivity.Keywords
This publication has 0 references indexed in Scilit: