Type of Document	Thesis
Author	Lackey, Hershel Hayes
URN	etd-01082011-141905
Title	ASYMMETRIC COPPER CATALYZED ADDITION TO ACTIVATED ALKENES
Degree	Master of Science
Department	Chemistry and Biochemistry, Department of
Advisory Committee	Advisor Name Title Tyler McQuade Committee Chair Greg B. Dudley Committee Member Lei Zhu Committee Member Michael Shatruk Committee Member
Keywords	Asymmetric Catalysis Borylation Copper NHC Organoboronates
Date of Defense	2010-12-03
Availability	unrestricted
Abstract This thesis presents the synthesis of a chiral 6-membered NHC catalyst copper catalyst and its use in the β-borylation and allylic substitution reactions. The application of the catalyst in the known β-borylation reaction demonstrates that the catalyst can provide high yields, enatioselectivities, and activity comparable if not improved to traditional 5-membered NHCs and phosphine copper complexes. The 6-membered NHC copper complex was then used in a nucleophilic diboron addition to allylic aryl ethers where the catalyst demonstrated different chemoselectivity compared to 5-membered NHC and phosphine catalyst. Further investigation of this phenomenon led to development of a stereoconvergent, asymmetric reaction which could convert mixtures of E and Z isomers into a single enantiomer in high yield.
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