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.
Department of Chemistry, Columbia University, New York, NY 10027, USA.
Xiaolun
X
Wang
Qinglin
Q
Meng
Andrew J
AJ
Nation
James L
JL
Leighton
D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D012821:Silanes / Q000737:chemistry*
D000438:Alcohols; D000447:Aldehydes; D012821:Silanes