Super Silyl Directing Groups: Highly Diastereoselective Aldol Reactions

Significance

Polyketides are an important class of natural products, and thus the development of ways to construct 1,3-polyol fragments represent a significant synthetic goal. A general methodology allowing 1,5-stereoinduction in the aldol reaction involving Mukaiyama products has not been developed so far. The authors have successfully used TMS- and TES-type super silyl groups to achieve complete 1,5-syn and -anti stereoselectivities. The obtained products could be reduced to 1,3,5-triols with syn and anti selectivity, thereby giving access to all the possible stereoisomers.