Enhancing Regiocontrol in Carboaluminations of Terminal Alkynes. Application to the One-Pot Synthesis of Coenzyme Q10
Organic Letters2007Vol. 9(19), pp. 3737–3740
Citations Over TimeTop 15% of 2007 papers
Abstract
Two new "generations" of methodological advances are reported for the Negishi carboalumination of terminal alkynes. Use of simple, inexpensive additives that alter the Al-Zr complex formed between Me(3)Al and Cp(2)ZrCl(2) give rise to an especially effective reagent mix that results in virtually complete control of regiochemistry upon carboalumination of 1-alkynes. One timely application to coenzyme Q10 is highlighted. Regioisomers from subsequent coupling, which would otherwise be very difficult to separate, are avoided.
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