Abstract
Starting from a polymer-bound olefin, iterative application of nitrile oxide 1,3-dipolar cycloaddition and selenide oxidation/elimination steps were employed to deliver a polymer-bound triisoxazoline that can be liberated from the resin by transesterification. When four nitroseleno ethers (2-5) and four capping nitroalkanes (6-9) were employed, a triisoxazoline library (V) of 64 positional isomers was obtained by three iterative applications of these two reactions. The tactical flexibility of this strategy for preparing small polyfunctional oligomers is particularly attractive in that each subunit addition proceeds via a C-C bond-forming step.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8755-8761 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 61 |
| Issue number | 25 |
| DOIs | |
| State | Published - Dec 13 1996 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Solid-phase combinatorial synthesis of polyisoxazolines : A two-reaction iterative protocol. / Kurth, Mark J.; Ahlberg Randall, Lisa A.; Takenouchi, Kazuya.
In: Journal of Organic Chemistry, Vol. 61, No. 25, 13.12.1996, p. 8755-8761.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Solid-phase combinatorial synthesis of polyisoxazolines
T2 - A two-reaction iterative protocol
AU - Kurth, Mark J.
AU - Ahlberg Randall, Lisa A.
AU - Takenouchi, Kazuya
PY - 1996/12/13
Y1 - 1996/12/13
N2 - Starting from a polymer-bound olefin, iterative application of nitrile oxide 1,3-dipolar cycloaddition and selenide oxidation/elimination steps were employed to deliver a polymer-bound triisoxazoline that can be liberated from the resin by transesterification. When four nitroseleno ethers (2-5) and four capping nitroalkanes (6-9) were employed, a triisoxazoline library (V) of 64 positional isomers was obtained by three iterative applications of these two reactions. The tactical flexibility of this strategy for preparing small polyfunctional oligomers is particularly attractive in that each subunit addition proceeds via a C-C bond-forming step.
AB - Starting from a polymer-bound olefin, iterative application of nitrile oxide 1,3-dipolar cycloaddition and selenide oxidation/elimination steps were employed to deliver a polymer-bound triisoxazoline that can be liberated from the resin by transesterification. When four nitroseleno ethers (2-5) and four capping nitroalkanes (6-9) were employed, a triisoxazoline library (V) of 64 positional isomers was obtained by three iterative applications of these two reactions. The tactical flexibility of this strategy for preparing small polyfunctional oligomers is particularly attractive in that each subunit addition proceeds via a C-C bond-forming step.
UR - http://www.scopus.com/inward/record.url?scp=0030474630&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0030474630&partnerID=8YFLogxK
U2 - 10.1021/jo961730l
DO - 10.1021/jo961730l
M3 - Article
AN - SCOPUS:0030474630
VL - 61
SP - 8755
EP - 8761
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 25
ER -