用于4-氨基四氢吡喃的三组分非对映选择性合成的樱井-普林斯-里特序列。
A Sakurai-Prins-Ritter sequence for the three-component diastereoselective synthesis of 4-amino tetrahydropyrans.
作者信息
Epstein Oleg L, Rovis Tomislav
机构信息
Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
出版信息
J Am Chem Soc. 2006 Dec 27;128(51):16480-1. doi: 10.1021/ja066794k.
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.
一种用于Sakurai-Prins-Ritter序列的简单一锅法，能够以高收率和优异的非对映选择性，从易得的4-乙酰氧基-1,3-二氧六环、烯丙基硅烷和腈快速组装4-酰氨基-2,6-取代的四氢吡喃。已证明多种腈可参与反应。非对映选择性始终很高，并且观察到的阳离子捕获立体化学遵循Alder的4-四氢吡喃基阳离子模型。
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