Strained silacycles in organic synthesis: the tandem aldol-allylation reaction

Allyl(crotyl)enolsilanes, when constrained in a five-membered ring with a 1,2-diol, react with aldehydes in a tandem aldol-allylation reaction to give polyketide fragments. These experimentally trivial and efficient reactions establish two new carbon-carbon bonds and up to four new stereocenters. The silane reagents, which owe their reactivity to strain release Lewis acidity, are easily prepared and stable to storage.     

Appendix addendum to ‘Congruence Normality’ of Alan Day

This work was partially supported by NSF Grant 87-03540.     

Small non-Arguesian lattices

Presented by R. McKenzie.