Abstract
"I took the road less traveled by and that has made all the difference." Not only fans of the poet Robert Frost recognize the attraction of the less common reaction path. Rather than the expected [3+2] cycloaddition, a novel ene-like cycloisomerization occurs on deprotonation of allyltrimethylsilyl - oxime compounds when the β-sp2 carbon atom of the allyltrimethylsilyl moiety is tethered to the oxime unit (see scheme). The resulting nitrile oxide functional group serves as an enophile, and the final cyclized product still has two functional groups suitable for further manipulations. TMS = SiMe3.
| Original language | English |
|---|---|
| Pages (from-to) | 1586-1588 |
| Number of pages | 3 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 41 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - May 3 2002 |
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Keywords
- Cycloisomerization
- Nitrile oxides
- Oximes
- Synthetic methods
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group. / Ishikawa, Teruhiko; Urano, Jin; Ikeda, Shushiro; Kobayashi, Yasuhiro; Saito, Seiki.
In: Angewandte Chemie - International Edition, Vol. 41, No. 9, 03.05.2002, p. 1586-1588.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Novel ene-like cycloisomerization reaction of nitrile oxides with a tethered allyltrimethylsilyl group
AU - Ishikawa, Teruhiko
AU - Urano, Jin
AU - Ikeda, Shushiro
AU - Kobayashi, Yasuhiro
AU - Saito, Seiki
PY - 2002/5/3
Y1 - 2002/5/3
N2 - "I took the road less traveled by and that has made all the difference." Not only fans of the poet Robert Frost recognize the attraction of the less common reaction path. Rather than the expected [3+2] cycloaddition, a novel ene-like cycloisomerization occurs on deprotonation of allyltrimethylsilyl - oxime compounds when the β-sp2 carbon atom of the allyltrimethylsilyl moiety is tethered to the oxime unit (see scheme). The resulting nitrile oxide functional group serves as an enophile, and the final cyclized product still has two functional groups suitable for further manipulations. TMS = SiMe3.
AB - "I took the road less traveled by and that has made all the difference." Not only fans of the poet Robert Frost recognize the attraction of the less common reaction path. Rather than the expected [3+2] cycloaddition, a novel ene-like cycloisomerization occurs on deprotonation of allyltrimethylsilyl - oxime compounds when the β-sp2 carbon atom of the allyltrimethylsilyl moiety is tethered to the oxime unit (see scheme). The resulting nitrile oxide functional group serves as an enophile, and the final cyclized product still has two functional groups suitable for further manipulations. TMS = SiMe3.
KW - Cycloisomerization
KW - Nitrile oxides
KW - Oximes
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=0037012719&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037012719&partnerID=8YFLogxK
U2 - 10.1002/1521-3773(20020503)41:9<1586::AID-ANIE1586>3.0.CO;2-M
DO - 10.1002/1521-3773(20020503)41:9<1586::AID-ANIE1586>3.0.CO;2-M
M3 - Article
C2 - 19750674
AN - SCOPUS:0037012719
VL - 41
SP - 1586
EP - 1588
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 9
ER -