207409-21-0Relevant academic research and scientific papers
Regioselective cyclizations utilizing a gold-catalyzed [3,3] propargyl ester rearrangement
Cran, John W.,Krafft, Marie E.
supporting information, p. 9398 - 9402 (2012/10/29)
Switch-Au-roo: A new strategy for the regioselective synthesis of unsaturated carbocycles by chemoselective activation of a Rauhut-Currier zwitterion surrogate, formed from the Au-catalyzed [3,3] sigmatropic rearrangement of propargylic esters, has been achieved. By reversing the regiochemistry of the propargyl ester the synthesis of either the endo- or exocyclic enones is feasible.
Intramolecular Simmons-Smith cyclopropanation. Studies into the reactivity of alkyl-substituted zinc carbenoids, effect of directing groups and synthesis of bicyclo[n.1.0]alkanes
Bull, James A.,Charette, Andre B.
supporting information; scheme or table, p. 1895 - 1902 (2010/04/25)
An intramolecular Simmons-Smith (IMSS) cyclopropanation has been developed, providing a novel method for the construction of substituted bicycloalkanes. First, functionalized gem-diiodoalkanes containing allylic alcohols were prepared in high yield. Then
Improved procedure for the synthesis of gem-diiodoalkanes by the alkylation of diiodomethane. Scope and limitations
Bull, James A.,Charette, Andre B.
, p. 8097 - 8100 (2008/12/22)
(Chemical Equation Presented) Functionalized gem-diiodoalkanes are obtained in good to excellent yields by employing a convenient modified procedure for the alkylation of NaCHI2 with alkyl iodides. Complete conversion to the diiodide is reliably obtained, avoiding a problematic separation of any remaining iodide starting material. Functional group tolerance toward olefins, acetals, ethers and silyl ethers, carbamates, and hindered esters is demonstrated. The use of an excess of LiCHI2 allows complete conversion of allyl and benzyl bromides with minimal elimination from the diiodide product.
