亲核卡宾催化环氧醛叠氮化反应合成1,2-氨基醇
Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.
作者信息
Vora Harit U, Moncecchi Johannah R, Epstein Oleg, Rovis Tomislav
机构信息
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
出版信息
J Org Chem. 2008 Dec 19;73(24):9727-31. doi: 10.1021/jo8020055.
Abstract
We report herein a nucleophilic carbene catalyzed redox azidation of epoxyaldehydes. The intermediate beta-hydroxy acyl azides undergo thermal Curtius rearrangement followed by trapping with excess azide to form carbamoyl azides or, in a complementary sequence, by the hydroxy group to form oxazolidinones. Both products are formed in modest to good yields and diastereoselectivities. The use of an enantioenriched triazolium catalyst leads to modest asymmetric induction.
摘要
我们在此报告亲核卡宾催化的环氧醛的氧化还原叠氮化反应。中间体β-羟基酰基叠氮化物经过热柯提斯重排，随后用过量叠氮化物捕获以形成氨基甲酰基叠氮化物，或者按照互补顺序，由羟基形成恶唑烷酮。两种产物均以中等至良好的产率和非对映选择性生成。使用对映体富集的三唑鎓催化剂会导致适度的不对称诱导。
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