Abstract
Three types of racemic [5]helicenyl acetates (1a, 2, and 3a) were synthesized. The synthesis of 2 was achieved by regioselective oxidation using o-iodoxybenzoic acid. The enzymatic kinetic resolution of 1a-3a was studied. The conversion with the highest rate and ee was obtained using 1a as the substrate and lipase Amano PS-IM as the enzyme. The two enantiomers of 1-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.
| Original language | English |
|---|---|
| Pages (from-to) | 6502-6508 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 80 |
| Issue number | 12 |
| DOIs | |
| Publication status | Published - Jun 19 2015 |
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All Science Journal Classification (ASJC) codes
- Organic Chemistry
Cite this
Synthesis and Resolution of Substituted [5]Carbohelicenes. / Usui, Kazuteru; Yamamoto, Kosuke; Shimizu, Takashi; Okazumi, Mieko; Mei, Biao; Demizu, Yosuke; Kurihara, Masaaki; Suemune, Hiroshi.
In: Journal of Organic Chemistry, Vol. 80, No. 12, 19.06.2015, p. 6502-6508.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and Resolution of Substituted [5]Carbohelicenes
AU - Usui, Kazuteru
AU - Yamamoto, Kosuke
AU - Shimizu, Takashi
AU - Okazumi, Mieko
AU - Mei, Biao
AU - Demizu, Yosuke
AU - Kurihara, Masaaki
AU - Suemune, Hiroshi
PY - 2015/6/19
Y1 - 2015/6/19
N2 - Three types of racemic [5]helicenyl acetates (1a, 2, and 3a) were synthesized. The synthesis of 2 was achieved by regioselective oxidation using o-iodoxybenzoic acid. The enzymatic kinetic resolution of 1a-3a was studied. The conversion with the highest rate and ee was obtained using 1a as the substrate and lipase Amano PS-IM as the enzyme. The two enantiomers of 1-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.
AB - Three types of racemic [5]helicenyl acetates (1a, 2, and 3a) were synthesized. The synthesis of 2 was achieved by regioselective oxidation using o-iodoxybenzoic acid. The enzymatic kinetic resolution of 1a-3a was studied. The conversion with the highest rate and ee was obtained using 1a as the substrate and lipase Amano PS-IM as the enzyme. The two enantiomers of 1-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.
UR - http://www.scopus.com/inward/record.url?scp=84935019143&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84935019143&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b00759
DO - 10.1021/acs.joc.5b00759
M3 - Article
AN - SCOPUS:84935019143
VL - 80
SP - 6502
EP - 6508
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 12
ER -