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

2010; Wiley; Volume: 49; Issue: 15 Linguagem: Inglês

10.1002/anie.200907076

1521-3773

Brian J. Albert, Hisashi Yamamoto,

Chemical Synthesis and Reactions

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.