The species on the zirconocene catalyst is changed from two Cp's to the Brintzinger ligand and catalytic amounts of MAO are used to usually effect a >99% regiocontrol of Negishi carboaluminations of 1-alkynes in toluene.
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Zirconium-Catalyzed Asymmetric Carboalumination of Unactivated Terminal Alkenes.
Acc Chem Res
October 2016
Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907, United States.
Carbometalation of alkenes with stereocontrol offers an important opportunity for asymmetric C-C bond formation. However, the scope of catalytic stereoselective carbometalation of alkenes had until recently been limited to electronically biased alkenes or those with the presence of directing groups or other auxiliary functionalities to overcome the challenge associated with regio- and stereoselectivity. Catalytic asymmetric carbometalation of unactivated alkenes on the other hand remained as a formidable challenge.
View Article and Find Full Text PDFEnhancing regiocontrol in carboaluminations of terminal alkynes. Application to the one-pot synthesis of coenzyme Q10.
Org Lett
September 2007
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, USA.
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.
View Article and Find Full Text PDFControlling regiochemistry in Negishi carboaluminations. Fine tuning the ligand on zirconium.
J Am Chem Soc
December 2006
Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA.
The species on the zirconocene catalyst is changed from two Cp's to the Brintzinger ligand and catalytic amounts of MAO are used to usually effect a >99% regiocontrol of Negishi carboaluminations of 1-alkynes in toluene.
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