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UBC Theses and Dissertations
Silver (I) catalyzed cycloisomerizations of enesulfonamides and enecarbamates Guieb, Krystle Dawn
Abstract
Eight substrates with the general structure 11.0 were synthesized. The substrates differed with respect to the heteroatom tether (X = oxygen or nitrogen), nitrogen protecting group (PG = p-toluenesulfonamide, tert-butylcarbamate, methyl carbamate), and substitution on the ring (Y = H or Ph). Silver (I)-catalyzed cycloisomerizations of the enesulfonamide and enecarbamate substrates successfully gave eight diene products ll.la-h in poor to good yields (36-81%). Diene ll.Ia was also further subjected to the Diels Alder reaction, with acrolein and methacrolein to give tricyclic cycloadducts 11.21a and 11.22a.
Item Metadata
| Title |
Silver (I) catalyzed cycloisomerizations of enesulfonamides and enecarbamates
|
| Creator | |
| Publisher |
University of British Columbia
|
| Date Issued |
2008
|
| Description |
Eight substrates with the general structure 11.0 were synthesized. The substrates
differed with respect to the heteroatom tether (X = oxygen or nitrogen), nitrogen
protecting group (PG = p-toluenesulfonamide, tert-butylcarbamate, methyl carbamate),
and substitution on the ring (Y = H or Ph). Silver (I)-catalyzed cycloisomerizations of
the enesulfonamide and enecarbamate substrates successfully gave eight diene products
ll.la-h in poor to good yields (36-81%). Diene ll.Ia was also further subjected to the
Diels Alder reaction, with acrolein and methacrolein to give tricyclic cycloadducts
11.21a and 11.22a.
|
| Extent |
6929874 bytes
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| Genre | |
| Type | |
| File Format |
application/pdf
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| Language |
eng
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| Date Available |
2009-03-05
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| Provider |
Vancouver : University of British Columbia Library
|
| Rights |
Attribution-NonCommercial-NoDerivatives 4.0 International
|
| DOI |
10.14288/1.0061712
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| URI | |
| Degree | |
| Program | |
| Affiliation | |
| Degree Grantor |
University of British Columbia
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| Graduation Date |
2008-11
|
| Campus | |
| Scholarly Level |
Graduate
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| Rights URI | |
| Aggregated Source Repository |
DSpace
|
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Rights
Attribution-NonCommercial-NoDerivatives 4.0 International