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