Enhancing regiocontrol in carboaluminations of terminal alkynes. Application to the one-pot synthesis of coenzyme Q10 |
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| Authors: | Lipshutz Bruce H Butler Tom Lower Asher Servesko Jeff |
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| Institution: | Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA. lipshutz@chem.ucsb.edu |
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| 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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