Abstract
Two stable and optically active iridium-salen complexes were synthesized by introducing a tolyl or phenyl ligand at the apical position, respectively, via the SEAr mechanism, and they were found to be efficient catalysts for cis-selective asymmetric cyclopropanation. The scope of the cyclopropanation was wide, and the reactions of not only conjugated mono-, di-, and trisubstituted olefins but also nonconjugated terminal olefins proceeded with high enantio- and cis-selectivity, even in the presence of a functional group such as an ether or ester. The utility of this cyclopropanation was demonstrated by a short step synthesis of 8-[(1R,2S)-2-hexylcyclopropyl]octanoate, isolated from Escherichia coli B-ATCC 11303, using the reaction as the key step.
| Original language | English |
|---|---|
| Pages (from-to) | 10327-10337 |
| Number of pages | 11 |
| Journal | Journal of the American Chemical Society |
| Volume | 130 |
| Issue number | 31 |
| DOIs | |
| Publication status | Published - Aug 6 2008 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
Cite this
Construction of aryliridium-salen complexes : Enantio- and cis-selective cyclopropanation of conjugated and nonconjugated olefins. / Suematsu, Hidehiro; Kanchiku, Shigefumi; Uchida, Tatsuya; Katsuki, Tsutomu.
In: Journal of the American Chemical Society, Vol. 130, No. 31, 06.08.2008, p. 10327-10337.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Construction of aryliridium-salen complexes
T2 - Enantio- and cis-selective cyclopropanation of conjugated and nonconjugated olefins
AU - Suematsu, Hidehiro
AU - Kanchiku, Shigefumi
AU - Uchida, Tatsuya
AU - Katsuki, Tsutomu
PY - 2008/8/6
Y1 - 2008/8/6
N2 - Two stable and optically active iridium-salen complexes were synthesized by introducing a tolyl or phenyl ligand at the apical position, respectively, via the SEAr mechanism, and they were found to be efficient catalysts for cis-selective asymmetric cyclopropanation. The scope of the cyclopropanation was wide, and the reactions of not only conjugated mono-, di-, and trisubstituted olefins but also nonconjugated terminal olefins proceeded with high enantio- and cis-selectivity, even in the presence of a functional group such as an ether or ester. The utility of this cyclopropanation was demonstrated by a short step synthesis of 8-[(1R,2S)-2-hexylcyclopropyl]octanoate, isolated from Escherichia coli B-ATCC 11303, using the reaction as the key step.
AB - Two stable and optically active iridium-salen complexes were synthesized by introducing a tolyl or phenyl ligand at the apical position, respectively, via the SEAr mechanism, and they were found to be efficient catalysts for cis-selective asymmetric cyclopropanation. The scope of the cyclopropanation was wide, and the reactions of not only conjugated mono-, di-, and trisubstituted olefins but also nonconjugated terminal olefins proceeded with high enantio- and cis-selectivity, even in the presence of a functional group such as an ether or ester. The utility of this cyclopropanation was demonstrated by a short step synthesis of 8-[(1R,2S)-2-hexylcyclopropyl]octanoate, isolated from Escherichia coli B-ATCC 11303, using the reaction as the key step.
UR - http://www.scopus.com/inward/record.url?scp=48749095700&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=48749095700&partnerID=8YFLogxK
U2 - 10.1021/ja802561t
DO - 10.1021/ja802561t
M3 - Article
C2 - 18613671
AN - SCOPUS:48749095700
VL - 130
SP - 10327
EP - 10337
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 31
ER -