A Triple-Aldol Cascade Reaction for the Rapid Assembly of Polyketides

Authors


  • This work was made possible by the generous support of NIH (P50 GM086 145-01) and the University of Chicago. We would additionally like to thank Antoni Jurkiewicz for his NMR expertise and Prof. V. V. Fokin for insightful discussions.

Abstract

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Triple play: The title reaction of 1 with simple aldehydes gives 3,5,7-trisilyloxy aldehydes in high yields and diastereoselectivities with extremely low catalyst loading (see scheme). Iodobenzene facilitates the third aldol reaction by apparently acting as a Lewis base towards the silyl catalyst. Tf=trifluoromethanesulfonyl.

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