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Use of α-chlorosulfides in indium promoted CC couplings
easy entry into the stereoselective formation of epoxy alkynes
Engstrom, G., Morelli, M., Palomo, C., & Mitzel, T. (1999). Use of α-chlorosulfides in indium promoted CC couplings: easy entry into the stereoselective formation of epoxy alkynes. Tetrahedron Letters, 40(33), 5967-5970. https://doi.org/10.1016/S0040-4039(99)01152-1
The use of α-chlorosulfide compounds to control stereoselectivity in indium promoted CC couplings occurs smoothly at room temperature under aqueous and mixed aqueous/organic conditions. Use of the halide to control syn/anti ratios simplifies the indium promoted coupling with respect to earlier studies and is used to gain entry into stereocontrolled epoxy alkynes in good yields.
Indium promoted reactions of aldehydes with novel indium nucleophiles obtained from α-chlorosulfides allows easy entry into stereoselective epoxy alkynes.