Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes

Novel bisisoquinoline-based ligands have been synthesized and used in various asymmetric reactions by Mr. Gao Qi in our lab. Good yields of up to 92% and moderate ee of up to 35% were obtained for the enantioselective conjugate addition of Grignard reagents to cyclohexenones to obtain the desired 1,...

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Main Author: Tee, Chin Yaw.
Other Authors: Zaher Judeh
Format: Final Year Project
Language:English
Published: 2009
Subjects:
Online Access:http://hdl.handle.net/10356/16424
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-164242023-03-03T15:36:37Z Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes Tee, Chin Yaw. Zaher Judeh School of Chemical and Biomedical Engineering DRNTU::Engineering::Chemical engineering::Chemicals and manufacture Novel bisisoquinoline-based ligands have been synthesized and used in various asymmetric reactions by Mr. Gao Qi in our lab. Good yields of up to 92% and moderate ee of up to 35% were obtained for the enantioselective conjugate addition of Grignard reagents to cyclohexenones to obtain the desired 1,4 – adducts. It was proposed to extend this investigation to the more challenging cyclopentenone substrates. Using cyclopentenone as a model substrate, various reaction parameters were optimized. These parameters include: Grignard reagent, chiral ligands, metal salts, solvent system, reaction temperature, catalyst loading and other components (such as molecular sieves and co-ligands) used. NMR was used to confirm the identity of the products while Gas Chromatography was used to determine the enantioselectivities of the desired products. Under the optimized reaction conditions investigated, the best ee of 28% was obtained for the reaction of 2-cyclopentenone with isopropylmagnesium chloride using 15 mol% of a complex between basic ligand M1 and copper (II) triflate in dry THF at -90 °C for 15 minutes in the presence of Drierite. Bachelor of Engineering (Chemical and Biomolecular Engineering) 2009-05-26T04:00:36Z 2009-05-26T04:00:36Z 2009 2009 Final Year Project (FYP) http://hdl.handle.net/10356/16424 en Nanyang Technological University 87 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Engineering::Chemical engineering::Chemicals and manufacture
spellingShingle DRNTU::Engineering::Chemical engineering::Chemicals and manufacture
Tee, Chin Yaw.
Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
description Novel bisisoquinoline-based ligands have been synthesized and used in various asymmetric reactions by Mr. Gao Qi in our lab. Good yields of up to 92% and moderate ee of up to 35% were obtained for the enantioselective conjugate addition of Grignard reagents to cyclohexenones to obtain the desired 1,4 – adducts. It was proposed to extend this investigation to the more challenging cyclopentenone substrates. Using cyclopentenone as a model substrate, various reaction parameters were optimized. These parameters include: Grignard reagent, chiral ligands, metal salts, solvent system, reaction temperature, catalyst loading and other components (such as molecular sieves and co-ligands) used. NMR was used to confirm the identity of the products while Gas Chromatography was used to determine the enantioselectivities of the desired products. Under the optimized reaction conditions investigated, the best ee of 28% was obtained for the reaction of 2-cyclopentenone with isopropylmagnesium chloride using 15 mol% of a complex between basic ligand M1 and copper (II) triflate in dry THF at -90 °C for 15 minutes in the presence of Drierite.
author2 Zaher Judeh
author_facet Zaher Judeh
Tee, Chin Yaw.
format Final Year Project
author Tee, Chin Yaw.
author_sort Tee, Chin Yaw.
title Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
title_short Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
title_full Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
title_fullStr Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
title_full_unstemmed Asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
title_sort asymmetric conjugate addition to enones catalyzed by novel bisisoquinoline/transition metal complexes
publishDate 2009
url http://hdl.handle.net/10356/16424
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