Titanium(IV)-promoted Mukaiyama aldol-Prins cyclizations |
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Authors: | Patterson Brian Marumoto Shinji Rychnovsky Scott D |
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Institution: | Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA. |
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Abstract: | reaction: see text] A new version of the Mukaiyama aldol-Prins (MAP) cyclization has been developed. Unsaturated enol ethers such as 3 were found to couple with aldehydes in the presence of TiBr(4) to give 4-bromotetrahydropyran products. This cascade reaction sequence leads to the formation of two new carbon-carbon bonds, a ring, and three new stereogenic centers. We expect this reaction to be a powerful new tool in synthesis. |
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