Formation of Five- and Seven-Membered Rings Enabled by the Triisopropylsilyl Auxiliary Group

A highly convenient synthetic pathway to 2-indanones from aldehydes was established. The introduction of a triisopropylsilyl group greatly facilitated Meinwald rearrangement of the intermediate epoxides and alleviated the necessity of polysubstitution for the clean formation of indenes and cyclopent...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 1; pp. 414 - 417
Main Authors Usanov, Dmitry L, Yamamoto, Hisashi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.01.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EPOXIDES
INDENE
CYCLIZATIONS
HOMOGENEOUS GOLD CATALYSIS
SUBSTITUTED BENZYLIC ALDEHYDES
EFFICIENT SYNTHESIS
PROMOTED SELECTIVE REARRANGEMENT
FRIEDEL-CRAFTS REACTION
STEREOSELECTIVE REARRANGEMENT
REGIOSELECTIVE REARRANGEMENT
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Summary:A highly convenient synthetic pathway to 2-indanones from aldehydes was established. The introduction of a triisopropylsilyl group greatly facilitated Meinwald rearrangement of the intermediate epoxides and alleviated the necessity of polysubstitution for the clean formation of indenes and cyclopentadienes via cyclodehydration of allylic alcohols; unprecedented freedom with respect to the product structure was thus achieved. The developed methodology could also be applicable to the formation of seven-membered rings leading to dibenzo[7]annulenes and dibenzosuberones.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol203209b