Catalytic enantioselective conjugate addition of metalated heteroaryl nucleophiles

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Title: Catalytic enantioselective conjugate addition of metalated heteroaryl nucleophiles
Author: Abbott, Lily Katherine
Abstract: This report details the discovery of a method for rhodium catalyzed asymmetric conjugate additions of heteroaryl nucleophiles to α -unsaturated carbonyl compounds . This work has successfully employed heteraryl titanates in enantioselective conjugate addition to α -unsaturated carbonyl compounds for the first time . Moreover , the utility of benzofuranyl , benzothiophenyl , and pyrrolo zinc reagents has been exemplified in enantioselective conjugate additions . We have found that the precatalyst [Rh (COD )acac] /OMeBIPHEP is broadly effective for enantioselective conjugate additions . Each heterocycle tested exhibited unique reactivity with respect to both conversion and enantioselectivity ; reactivities of heteroaryl zinc reagents and heteroaryl titanates in enantioselective conjugate additions to α -unsaturated carbonyl compounds are sometimes complementary . Efforts directed towards the development of a method for rhodium -free enantioselective conjugate addition of furan to α -unsaturated carbonyl compounds are also described .
URI: http : / /hdl .handle .net /2152 /ETD -UT -2010 -05 -1466
Date: 2010-11-05

Citation

Catalytic enantioselective conjugate addition of metalated heteroaryl nucleophiles. Master's thesis, University of Texas at Austin. Available electronically from http : / /hdl .handle .net /2152 /ETD -UT -2010 -05 -1466 .

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