Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions
碩士 === 國立清華大學 === 化學系 === 99 === This thesis reports the asymmetric tandem reaction using 1,3-dioxolan-4-one 14. At first, Michael reaction of the enolate from 1,3-dioxolan-4-one 14 with methyl crotonate afforded product 20b with two contiguous chiral centers. Compound 20b underwent α-substitution r...
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ndltd-TW-099NTHU50650812015-10-13T20:23:00Z http://ndltd.ncl.edu.tw/handle/73625169444175313329 Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions 樟腦磺醯胺衍生物之掌性1,3-二?環戊-4-酮化合物於不對稱串聯反應之研究 Liao, Hao-Chun 廖浩淳 碩士 國立清華大學 化學系 99 This thesis reports the asymmetric tandem reaction using 1,3-dioxolan-4-one 14. At first, Michael reaction of the enolate from 1,3-dioxolan-4-one 14 with methyl crotonate afforded product 20b with two contiguous chiral centers. Compound 20b underwent α-substitution reaction and generated the third chiral center. The first Michael reaction gave a single product in 82% yield, and the second reaction afforded product with high diastereoselectivity(up to 80.4/1.8) in 53-83% yield. Enolate of 1,3-dioxolan-4-one 14 reacted with methyl tiglate and, after the treatment with chiral compound 33 as proton source, afforded single product 31 in 64% yield. Uang, Biing-Jiun 汪炳鈞 2011 學位論文 ; thesis 100 zh-TW |
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碩士 === 國立清華大學 === 化學系 === 99 === This thesis reports the asymmetric tandem reaction using 1,3-dioxolan-4-one 14. At first, Michael reaction of the enolate from 1,3-dioxolan-4-one 14 with methyl crotonate afforded product 20b with two contiguous chiral centers. Compound 20b underwent α-substitution reaction and generated the third chiral center. The first Michael reaction gave a single product in 82% yield, and the second reaction afforded product with high diastereoselectivity(up to 80.4/1.8) in 53-83% yield. Enolate of 1,3-dioxolan-4-one 14 reacted with methyl tiglate and, after the treatment with chiral compound 33 as proton source, afforded single product 31 in 64% yield.
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author2 |
Uang, Biing-Jiun |
author_facet |
Uang, Biing-Jiun Liao, Hao-Chun 廖浩淳 |
author |
Liao, Hao-Chun 廖浩淳 |
spellingShingle |
Liao, Hao-Chun 廖浩淳 Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions |
author_sort |
Liao, Hao-Chun |
title |
Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions |
title_short |
Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions |
title_full |
Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions |
title_fullStr |
Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions |
title_full_unstemmed |
Applications of N,N-Diisopropyl-10-camphorsulfonamide Derived Chiral 1,3-Dioxolanes in Asymmetric Tandem Reactions |
title_sort |
applications of n,n-diisopropyl-10-camphorsulfonamide derived chiral 1,3-dioxolanes in asymmetric tandem reactions |
publishDate |
2011 |
url |
http://ndltd.ncl.edu.tw/handle/73625169444175313329 |
work_keys_str_mv |
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