Enhanced diastereoselectivity in asymmetric crotylation reactions using propargylic dicobalt hexacarbonyl complexes |
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Authors: | Sui M Panek J S |
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Institution: | Department of Chemistry, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, MA 02215, USA. |
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Abstract: | reaction: see text] Hexacarbonyl dicobalt complexes of propargylic acetals undergo Lewis acid catalyzed crotylation reactions with enhanced levels of diastereoselectivity (dr 6 to >20:1, syn/anti) while efficiently producing stereochemically well-defined homoallylic ethers. These results are in contrast to uncomplexed propargylic acetals, which undergo the crotylation reactions with low selectivity (dr < 2:1, syn/anti). After removal of the cobalt complex, the reactions afford propargylic ethers in high yields. |
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