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Facile Access to Versatile Polyaromatic Building Blocks: Selectively Protected Benzocyclobutenedione Derivatives via Regioselective [2+2] Cycloaddition of α ‐Alkoxybenzyne and Ketene Silyl Acetal
Author(s) -
Hamura Toshiyuki,
Hosoya Takamitsu,
Yamaguchi Hiroki,
Kuriyama Yokusu,
Tanabe Mitsujiro,
Miyamoto Makoto,
Yasui Yoshizumi,
Matsumoto Takashi,
Suzuki Keisuke
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200211)85:11<3589::aid-hlca3589>3.0.co;2-z
Subject(s) - ketene , chemistry , regioselectivity , cycloaddition , silylation , acetal , structural isomer , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
A facile, divergent access to highly oxygenated benzocyclobutene derivatives was developed via the regioselective [2+2] cycloaddition of α ‐alkoxybenzynes and ketene silyl acetals. The cycloadducts could be converted to selectively protected alkoxybenzocyclobutenediones, an attractive class of compounds for the synthesis of polyaromatic compounds. As one possible application, divergent access to a regioisomer pair of sulfonylphthalides for the Hauser approach to polyaromatic compounds is described.