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Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffoldsElectronic supplementary information (ESI) available: Experimental details and characterisation data for compounds 11, 17-19, 23-26, azides 27a-h, and spiroacetal-triazoles 28a-h and 10a-h. 1H and 13C NMR spectra of all new compounds. See DOI: 10.1039/c2ob06802hThis article is part of the Organic & Biomolecular Chemistry 10th Anniversary issue
The enantioselective synthesis of novel C -linked spiroacetal-triazoles 10 is reported. The key step involves reaction of acetylenic spiroacetal 11 with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold 11 was prepared from si...
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| creator | Kueh, Jui Thiang Brian Choi, Ka Wai Brimble, Margaret A |
| description | The enantioselective synthesis of novel
C
-linked spiroacetal-triazoles
10
is reported. The key step involves reaction of acetylenic spiroacetal
11
with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold
11
was prepared from silyl-protected Weinreb amide
19
using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.
The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC) affords novel
C
-linked spiroacetal-triazoles. The anomeric
C
-linkage is anticipated to provide increased stability towards hydrolytic cleavage. |
| doi_str_mv | 10.1039/c2ob06802h |
| format | article |
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C
-linked spiroacetal-triazoles
10
is reported. The key step involves reaction of acetylenic spiroacetal
11
with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold
11
was prepared from silyl-protected Weinreb amide
19
using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.
The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC) affords novel
C
-linked spiroacetal-triazoles. The anomeric
C
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C
-linked spiroacetal-triazoles
10
is reported. The key step involves reaction of acetylenic spiroacetal
11
with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold
11
was prepared from silyl-protected Weinreb amide
19
using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.
The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC) affords novel
C
-linked spiroacetal-triazoles. The anomeric
C
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C
-linked spiroacetal-triazoles
10
is reported. The key step involves reaction of acetylenic spiroacetal
11
with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold
11
was prepared from silyl-protected Weinreb amide
19
using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.
The union of the biologically privileged 6,6-spiroacetal scaffold with azides by the regioselective Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC) affords novel
C
-linked spiroacetal-triazoles. The anomeric
C
-linkage is anticipated to provide increased stability towards hydrolytic cleavage.</abstract><doi>10.1039/c2ob06802h</doi><tpages>1</tpages></addata></record> |
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| source | Royal Society of Chemistry |
| title | Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffoldsElectronic supplementary information (ESI) available: Experimental details and characterisation data for compounds 11, 17-19, 23-26, azides 27a-h, and spiroacetal-triazoles 28a-h and 10a-h. 1H and 13C NMR spectra of all new compounds. See DOI: 10.1039/c2ob06802hThis article is part of the Organic & Biomolecular Chemistry 10th Anniversary issue |
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