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Synlett 2002(11): 1868-1870
DOI: 10.1055/s-2002-34871
LETTER
© Georg Thieme Verlag Stuttgart · New York

Novel Isobenzofuran Generation from Silylated Lactol Leading to Desilylated or Silylated Adducts Depending on the Choice of Metal Fluorides

Hirofumi Ohmura, Koichi Mikami*
Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo, 152-8552, Japan
Fax: +81(3)57342776; e-Mail: kmikami@o.cc.titech.ac.jp;
Further Information

Publication History

Received 10 August 2002
Publication Date:
21 October 2002 (online)

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Abstract

A new method of isobenzofuran generation was developed by treating silylated lactol with metal fluorides. The reactions with hard early transition metal fluorides gave de-silylated dimethyl acetylenedicarboxylate (DMAD) adduct mainly. By contrast, the silyl-retained DMAD adduct, which could be used for further transformation, was also obtained depending on the choice of metal fluorides such as lanthanoides or low valent transition metal fluor­ides.

Key words

isobenzofuran - carbonyl ylides - silylated lactol - silylated isobenzofuran adducts - metal fluorides

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