Abstract
Treatment of N-tosyliodoaziridine derivatives with Et3B efficiently produces various azahomoallyl radical (2-akenylamidyl radical) species which give oxygen-functionalized pyrrolidine derivatives through iodine atom transfer [3 + 2] cycloaddition with electron-rich alkenes such as enol ethers and ketene acetal. The present cycloaddition reaction proceeds regioselectively via C-N bond cleavage of an aziridinylalkyl radical intermediate and addition of the resulting azahomoallyl radicals to the terminal carbon of an alkene. The reaction of alkenes with the cyclohexenylamidyl radical generated from an optically active bicyclic iodoaziridine [(1S,2S,6S)-2-iodo-7-(p-toluenesulfonyl)-7-azabicyclo[4.1.0]heptane, 94% eel also proceeds to give optically active octahydroindole derivatives (84-93% ee).
| Original language | English |
|---|---|
| Pages (from-to) | 3184-3189 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 68 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2003 Apr 18 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Iodine atom transfer [3 + 2] cycloaddition reaction with electron-rich alkenes using N-tosyliodoaziridine derivatives as novel azahomoallyl radical precursors. / Kitagawa, Osamu; Miyaji, Shinsaku; Yamada, Yoichiro; Fujiwara, Hiroki; Taguchi, Takeo.
In: Journal of Organic Chemistry, Vol. 68, No. 8, 18.04.2003, p. 3184-3189.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Iodine atom transfer [3 + 2] cycloaddition reaction with electron-rich alkenes using N-tosyliodoaziridine derivatives as novel azahomoallyl radical precursors
AU - Kitagawa, Osamu
AU - Miyaji, Shinsaku
AU - Yamada, Yoichiro
AU - Fujiwara, Hiroki
AU - Taguchi, Takeo
PY - 2003/4/18
Y1 - 2003/4/18
N2 - Treatment of N-tosyliodoaziridine derivatives with Et3B efficiently produces various azahomoallyl radical (2-akenylamidyl radical) species which give oxygen-functionalized pyrrolidine derivatives through iodine atom transfer [3 + 2] cycloaddition with electron-rich alkenes such as enol ethers and ketene acetal. The present cycloaddition reaction proceeds regioselectively via C-N bond cleavage of an aziridinylalkyl radical intermediate and addition of the resulting azahomoallyl radicals to the terminal carbon of an alkene. The reaction of alkenes with the cyclohexenylamidyl radical generated from an optically active bicyclic iodoaziridine [(1S,2S,6S)-2-iodo-7-(p-toluenesulfonyl)-7-azabicyclo[4.1.0]heptane, 94% eel also proceeds to give optically active octahydroindole derivatives (84-93% ee).
AB - Treatment of N-tosyliodoaziridine derivatives with Et3B efficiently produces various azahomoallyl radical (2-akenylamidyl radical) species which give oxygen-functionalized pyrrolidine derivatives through iodine atom transfer [3 + 2] cycloaddition with electron-rich alkenes such as enol ethers and ketene acetal. The present cycloaddition reaction proceeds regioselectively via C-N bond cleavage of an aziridinylalkyl radical intermediate and addition of the resulting azahomoallyl radicals to the terminal carbon of an alkene. The reaction of alkenes with the cyclohexenylamidyl radical generated from an optically active bicyclic iodoaziridine [(1S,2S,6S)-2-iodo-7-(p-toluenesulfonyl)-7-azabicyclo[4.1.0]heptane, 94% eel also proceeds to give optically active octahydroindole derivatives (84-93% ee).
UR - http://www.scopus.com/inward/record.url?scp=0037453567&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0037453567&partnerID=8YFLogxK
U2 - 10.1021/jo0266846
DO - 10.1021/jo0266846
M3 - Article
C2 - 12688789
AN - SCOPUS:0037453567
VL - 68
SP - 3184
EP - 3189
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 8
ER -