Diastereoselective Spiroketalization: Stereocontrol Using An Iron(0) Tricarbonyl Diene Complex

It has been demonstrated that an element of planar chirality can influence the formation of an adjacent spiroketal stereocenter. Appropriately functionalized enantiomerically pure 1- and 2-sulfinyl 1,3-dien-5-ones and their corresponding iron(0) tricarbonyl complexes (7, 17) have been prepared, and...

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Bibliographic Details
Published in:Organic letters 2011-01, Vol.13 (1), p.58-61
Main Authors: Paley, Robert S, Laupheimer, Madeleine C, Erskine, Nathaniel A. K, Rablen, Paul R, Pike, Robert D, Jones, James S
Format: Article
Language:English
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Summary:It has been demonstrated that an element of planar chirality can influence the formation of an adjacent spiroketal stereocenter. Appropriately functionalized enantiomerically pure 1- and 2-sulfinyl 1,3-dien-5-ones and their corresponding iron(0) tricarbonyl complexes (7, 17) have been prepared, and the derived spiroketals (8, 18) are made in good to excellent diastereoselectivity. A preliminary exploration of the combined effects of planar and central chirality upon the diastereoselectivity revealed matched and mismatched combinations (14).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102472g