A Sakurai-Prins-Ritter sequence for the three-component diastereoselective synthesis of 4-amino tetrahydropyrans.
A simple one-pot procedure for the Sakurai-Prins-Ritter sequence allows rapid assembly of 4-acylamino-2,6-substituted tetrahydropyrans in high yields and with excellent diastereoselectivity from readily available 4-acetoxy-1,3-dioxanes, allylsilanes, and nitriles. A variety of nitriles have been shown to participate. Diastereoselectivities are uniformly high and observed stereochemistry of cation trapping proceeds according to Alder's model of the 4-tetrahydropyranyl cation.
Epstein
Oleg L
OL
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Rovis
Tomislav
T
D008968:Molecular Conformation; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011714:Pyrans