抄録
A concise procedure to prepare optically active (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol was developed. Ethyl (E)-3-iodoacrylate was converted to racemic (E)-1-iodohexa-1,5-dien-3-ol under flow and batch conditions via successive half reduction followed by Grignard reaction. Kinetic resolution of the racemic alcohol was achieved under flow conditions by using lipase packed in a column to afford (3S)-(E)-1-iodohexa-1,5-dien-3-ol and corresponding (3R)-acetate. Removal of the acetyl group was also carried out under flow conditions by using ion exchange resin packed in a column and (3R)-(E)-1-iodohexa-1,5-dien-3-ol was obtained after simple evaporation of the eluent.
| 元の言語 | 英語 |
|---|---|
| ページ（範囲） | 1116-1118 |
| ページ数 | 3 |
| ジャーナル | Chemistry Letters |
| 巻 | 47 |
| 発行部数 | 9 |
| DOI | |
| 出版物ステータス | 出版済み - 1 1 2018 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
これを引用
Flow synthesis of (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol : Chiral building blocks for natural product synthesis. / Katayama, Sota; Koge, Tomoyuki; Katsuragi, Satoko; Akai, Shuji; Oishi, Tohru.
：: Chemistry Letters, 巻 47, 番号 9, 01.01.2018, p. 1116-1118.研究成果: ジャーナルへの寄稿 › 記事
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TY - JOUR
T1 - Flow synthesis of (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol
T2 - Chiral building blocks for natural product synthesis
AU - Katayama, Sota
AU - Koge, Tomoyuki
AU - Katsuragi, Satoko
AU - Akai, Shuji
AU - Oishi, Tohru
PY - 2018/1/1
Y1 - 2018/1/1
N2 - A concise procedure to prepare optically active (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol was developed. Ethyl (E)-3-iodoacrylate was converted to racemic (E)-1-iodohexa-1,5-dien-3-ol under flow and batch conditions via successive half reduction followed by Grignard reaction. Kinetic resolution of the racemic alcohol was achieved under flow conditions by using lipase packed in a column to afford (3S)-(E)-1-iodohexa-1,5-dien-3-ol and corresponding (3R)-acetate. Removal of the acetyl group was also carried out under flow conditions by using ion exchange resin packed in a column and (3R)-(E)-1-iodohexa-1,5-dien-3-ol was obtained after simple evaporation of the eluent.
AB - A concise procedure to prepare optically active (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol was developed. Ethyl (E)-3-iodoacrylate was converted to racemic (E)-1-iodohexa-1,5-dien-3-ol under flow and batch conditions via successive half reduction followed by Grignard reaction. Kinetic resolution of the racemic alcohol was achieved under flow conditions by using lipase packed in a column to afford (3S)-(E)-1-iodohexa-1,5-dien-3-ol and corresponding (3R)-acetate. Removal of the acetyl group was also carried out under flow conditions by using ion exchange resin packed in a column and (3R)-(E)-1-iodohexa-1,5-dien-3-ol was obtained after simple evaporation of the eluent.
UR - http://www.scopus.com/inward/record.url?scp=85052371662&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85052371662&partnerID=8YFLogxK
U2 - 10.1246/cl.180475
DO - 10.1246/cl.180475
M3 - Article
AN - SCOPUS:85052371662
VL - 47
SP - 1116
EP - 1118
JO - Chemistry Letters
JF - Chemistry Letters
SN - 0366-7022
IS - 9
ER -