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Published on: August 1, 2018
Lewis Acid Catalyzed Ring-Opening 1,3-Aminothiolation of Donor-Acceptor Cyclopropanes Using Sulfenamides
Avishek Guin1, Thukaram Rathod1, Rahul N Gaykar1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Abstract:
Yb(OTf)3 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.
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