Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 14, Pages 2488-2492Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b806243a
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We have developed a direct amine/acid-catalyzed stereoselective hydrogenation of a variety of Wieland-Miescher (W-M) ketones, Hajos-Parrish (H-P) ketones and their analogs with organic hydrides (Hantzsch esters) as the hydrogen source. This astonishingly simple and biomimetic approach was used to construct highly functionalized chiral bicyclo[4.4.0] decane1,6-diones 6 in a diastereoselective fashion. This is an example of the development of a new technology by the combination of multiple catalysts and components in one pot to deliver highly functionalized chiral molecules.
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