Asymmetric Intermolecular Pauson−Khand Reactions of Unstrained Olefins: The (o-Dimethylamino)phenylsulfinyl Group as an Efficient Chiral Auxiliary
- 14 November 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (49) , 14992-14993
- https://doi.org/10.1021/ja038491l
Abstract
The first asymmetric version of intermolecular Pauson-Khand reactions of unstrained alkenes is described. Generally simple acyclic alkenes exhibit low reactivity and regioselectivity in intermolecular Pauson-Khand reactions; however, o-(dimethylamino)phenyl vinyl sulfoxide reacts under very mild conditions with a wide variety of terminal alkynes in a completely regioselective and highly stereoselective manner. The utility of the resulting 5-sulfinyl-2-cyclopentenones in asymmetric synthesis is illustrated by a very short enantioselective synthesis of the antibiotic (-)-pentenomycin I.Keywords
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