Improved method for the synthesis of (E)-cyclic-β-alkoxyacrylates under mild conditions

✍ Scribed by Keisuke Kato; Akira Nishimura; Yasuhiro Yamamoto; Hiroyuki Akita

• Book ID: 104230755
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 61 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00689-x

✦ Synopsis

The oxidative cyclization-methoxycarbonylation of cyclic-and acyclic-4-yn-1-ols 1 in the presence of Pd(II)/p-benzoquinone in methanol at 0°C under a carbon monoxide atmosphere (balloon) afforded (E)-cyclic-b-alkoxyacrylates 2 in good to excellent yields. The present reaction is applicable to the above-mentioned substrates bearing the additional functional groups such as acetate, hydroxyl, ketone, ester, terminal acetylene and the acid-sensitive protecting groups (TBDPS, TBDMS, MOM and THP). A new synthesis of the left part of the cystothiazoles is presented.