Guin Avishek, Rathod Thukaram, Gaykar Rahul N, Roy Tony, Biju Akkattu T
Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Org Lett. 2020 Mar 20;22(6):2276-2280. doi: 10.1021/acs.orglett.0c00483. Epub 2020 Mar 4.
Yb(OTf) catalyzed mild and regioselective ring-opening 1,3-aminothiolation of donor-acceptor (D-A) cyclopropanes using sulfenamides has been demonstrated. The insertion of the C-C σ-bond of D-A cyclopropanes into the S-N σ-bond of sulfenamides allows the synthesis of diverse γ-aminated α-thiolated malonic diesters in moderate to good yields (up to 87%) with good functional group compatibility. The stereospecificity of the reaction was demonstrated using enantiomerically pure D-A cyclopropane.
已证明Yb(OTf)催化供体-受体（D-A）环丙烷与亚磺酰胺进行温和且区域选择性的开环1,3-氨基硫醇化反应。D-A环丙烷的C-C σ键插入亚磺酰胺的S-N σ键中，能够以中等至良好的产率（高达87%）合成多种γ-氨基化α-硫醇化丙二酸二酯，且具有良好的官能团兼容性。使用对映体纯的D-A环丙烷证明了该反应的立体专一性。
