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

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1116-1118
Number of pages3
JournalChemistry Letters
Volume47
Issue number9
DOIs
Publication statusPublished - Jan 1 2018

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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