Abstract
An efficient, transition metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI-tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor.
| Original language | English |
|---|---|
| Pages (from-to) | 5895-5898 |
| Number of pages | 4 |
| Journal | Chemistry (Weinheim an der Bergstrasse, Germany) |
| Volume | 20 |
| Issue number | 20 |
| DOIs | |
| Publication status | Published - 12 May 2014 |
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Keywords
- cyclopropanation reactions
- hypoiodous acid
- iodine
- oxidation
- small ring systems
ASJC Scopus subject areas
- Medicine(all)
Cite this
Hypoiodite-mediated cyclopropanation of alkenes. / Yoshimura, Akira; Koski, Steven R.; Kastern, Brent J.; Fuchs, Jonathan M.; Jones, T. Nicholas; Yusubova, Roza Y.; Nemykin, Victor N.; Zhdankin, Viktor Vladimirovich.
In: Chemistry (Weinheim an der Bergstrasse, Germany), Vol. 20, No. 20, 12.05.2014, p. 5895-5898.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Hypoiodite-mediated cyclopropanation of alkenes
AU - Yoshimura, Akira
AU - Koski, Steven R.
AU - Kastern, Brent J.
AU - Fuchs, Jonathan M.
AU - Jones, T. Nicholas
AU - Yusubova, Roza Y.
AU - Nemykin, Victor N.
AU - Zhdankin, Viktor Vladimirovich
PY - 2014/5/12
Y1 - 2014/5/12
N2 - An efficient, transition metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI-tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor.
AB - An efficient, transition metal-free procedure for the cyclopropanation of alkenes using malononitrile and the LiI-tBuOCl combination under mild reaction conditions is described. The reaction mechanism most likely involves tBuOI generated in situ from LiI and tBuOCl. The utility of this new methodology has been demonstrated by the synthesis of a potential HIV-1 RT inhibitor.
KW - cyclopropanation reactions
KW - hypoiodous acid
KW - iodine
KW - oxidation
KW - small ring systems
UR - http://www.scopus.com/inward/record.url?scp=84928213286&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84928213286&partnerID=8YFLogxK
U2 - 10.1002/chem.201402372
DO - 10.1002/chem.201402372
M3 - Article
VL - 20
SP - 5895
EP - 5898
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 20
ER -