Abstract
An efficient cycloaddition of heterocyclic alkenes with nitrile oxides generated in situ from the corresponding aldoximes using organohypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (Koser's reagent), has been developed. The oxidative cyclization of various aldoximes with 1-propene-1,3-sultone affords the respective isoxazoline-ring-fused heterobicyclic products in moderate to good yields. Furthermore, the reaction of aldoxime with a cyclic phospholene-oxide under similar conditions produces the corresponding heterobicyclic phospholene oxides in moderate yields. The structures of bicyclic phospholene oxide and two sultones were established by single-crystal X-ray crystallography.
| Original language | English |
|---|---|
| Pages (from-to) | 11742-11751 |
| Number of pages | 10 |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - 17 Nov 2017 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes. / Yoshimura, Akira; Nguyen, Khiem C.; Rohde, Gregory T.; Postnikov, Pavel S.; Yusubov, Mekhman S.; Zhdankin, Viktor V.
In: Journal of Organic Chemistry, Vol. 82, No. 22, 17.11.2017, p. 11742-11751.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Hypervalent Iodine Reagent Mediated Oxidative Heterocyclization of Aldoximes with Heterocyclic Alkenes
AU - Yoshimura, Akira
AU - Nguyen, Khiem C.
AU - Rohde, Gregory T.
AU - Postnikov, Pavel S.
AU - Yusubov, Mekhman S.
AU - Zhdankin, Viktor V.
PY - 2017/11/17
Y1 - 2017/11/17
N2 - An efficient cycloaddition of heterocyclic alkenes with nitrile oxides generated in situ from the corresponding aldoximes using organohypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (Koser's reagent), has been developed. The oxidative cyclization of various aldoximes with 1-propene-1,3-sultone affords the respective isoxazoline-ring-fused heterobicyclic products in moderate to good yields. Furthermore, the reaction of aldoxime with a cyclic phospholene-oxide under similar conditions produces the corresponding heterobicyclic phospholene oxides in moderate yields. The structures of bicyclic phospholene oxide and two sultones were established by single-crystal X-ray crystallography.
AB - An efficient cycloaddition of heterocyclic alkenes with nitrile oxides generated in situ from the corresponding aldoximes using organohypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (Koser's reagent), has been developed. The oxidative cyclization of various aldoximes with 1-propene-1,3-sultone affords the respective isoxazoline-ring-fused heterobicyclic products in moderate to good yields. Furthermore, the reaction of aldoxime with a cyclic phospholene-oxide under similar conditions produces the corresponding heterobicyclic phospholene oxides in moderate yields. The structures of bicyclic phospholene oxide and two sultones were established by single-crystal X-ray crystallography.
UR - http://www.scopus.com/inward/record.url?scp=85034618079&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85034618079&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b01462
DO - 10.1021/acs.joc.7b01462
M3 - Article
AN - SCOPUS:85034618079
VL - 82
SP - 11742
EP - 11751
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -