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Moriya, Kohei; Schwärzer, Kuno; Karaghiosoff, Konstantin; Knochel, Paul (2016): Stereoselective Synthesis of Secondary Alkyllithiums and Their Application to Stereoselective Cuprations or Intramolecular Carbolithiations for the Stereoselective Synthesis of Alkylidene-cyclobutanes. In: Synthesis-Stuttgart, Vol. 48, No. 19: pp. 3141-3154
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Secondary alkyllithium reagents were prepared stereoselectively via an iodo-lithium exchange by using tert-butyllithium. The resulting secondary alkyllithiums were converted directly into the corresponding alkylcopper reagents by transmetalation with copper(I) bromide-triethyl phosphite [CuBr center dot P(OEt)(3)] with retention of configuration and without significant loss of stereoselectivity. The resulting alkylcopper reagents were used for carbocupration or acylation reactions. In addition, a new intramolecular carbolithiation of secondary alkyllithium reagents possessing a remote alkyne moiety was also investigated, allowing the stereoselective production of alkylidenecylobutane derivatives with very high stereocontrol.