Beilstein J. Org. Chem.2008,4, No. 17, doi:10.3762/bjoc.4.17
propynoates at room temperature to yield the corresponding adducts in moderate to excellent yields.
Background
Compounds with a monofluoromethyl moiety are of great importance with regards to isostere-based drugdesign [1][2][3][4]. Consequently, synthesis of new functionalized α-monofluorine-substituted
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Graphical Abstract
Scheme 1:
Reaction mechanism for phosphine catalyzed 1,4-addition to α,β-unsaturated compounds.
Beilstein J. Org. Chem.2006,2, No. 16, doi:10.1186/1860-5397-2-16
, and their estrogenic and other physiological properties, making them promising lead compounds for drugdesign.
Results
The reduction of isoflavones by various hydride reagents occurs by a 1,4-pathway in contrast to ordinary β-alkoxy-α,β-unsaturated ketones. Isoflavan-4-ones, cis- and trans-isoflavan-4