A Sakurai−Prins−Ritter Sequence for the Three-Component Diastereoselective Synthesis of 4-Amino Tetrahydropyrans
Journal of the American Chemical Society2006Vol. 128(51), pp. 16480–16481
Citations Over TimeTop 10% of 2006 papers
Abstract
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.
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