Flow synthesis of (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol: Chiral building blocks for natural product synthesis

Sota Katayama, Tomoyuki Koge, Satoko Katsuragi, Shuji Akai, Tohru Oishi

研究成果: ジャーナルへの寄稿記事

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
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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Ion Exchange Resins
Biological Products
Lipase
Evaporation
Acetates
Alcohols
Kinetics

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

Katayama, Sota ; Koge, Tomoyuki ; Katsuragi, Satoko ; Akai, Shuji ; Oishi, Tohru. / Flow synthesis of (3R)- and (3S)-(E)-1-iodohexa-1,5-dien-3-ol : Chiral building blocks for natural product synthesis. :: Chemistry Letters. 2018 ; 巻 47, 番号 9. pp. 1116-1118.
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abstract = "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.",
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AU - Oishi, Tohru

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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.

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