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Title: Theoretical and experimental investigation of stereoselective iodolactonisation
Author: Bissmire, Stewart
ISNI:       0000 0004 2749 7598
Awarding Body: Cardiff University
Current Institution: Cardiff University
Date of Award: 2006
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Lactonizations are important steps in many synthetic sequences. Substrate-controlled reactions that use chiral auxiliaries or chiral alkenes have already been studied in depth. This study focuses on stereoselective reagent-controlled iodolactonizations, by application of a new method that uses complexes of iodine monochloride and various donor molecules. (/)-l,2,3,4-Tetrahydro-l-naphthylamine and other amines with similar structures were synthesized and found to be efficient in the iodocyclization of 4-aryl-4-pentenoic acids and other similar substrates. Calculations were performed on complexes of ( )-l,2,3,4-tetrahydro-l-naphthylamine with XC1 (X=I, H) to identify possible reactive species in these iodocyclizations. Various levels of theory were employed, including B3LYP/6-31+G (d,p) using a modified SDD basis set for iodine.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available