Lewis Acid Promoted Reactions of 1,1-Diarylallenes and Ketone Derivatives: Synthesis of Indenes by an Addition/Cyclization Reaction

Shoko Yamazaki; Yugo Fukushima; Tetsuma Ukai; Kohei Tatsumi; Akiya Ogawa

doi:10.1055/s-0031-1290776

Synthesis, Table of Contents

Synthesis 2012; 44(14): 2155-2161
DOI: 10.1055/s-0031-1290776

special topic

Lewis Acid Promoted Reactions of 1,1-Diarylallenes and Ketone Derivatives: Synthesis of Indenes by an Addition/Cyclization Reaction

Authors

Shoko Yamazaki*

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
Yugo Fukushima

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan, Fax: +81(742)279289 Email: yamazaks@nara-edu.ac.jp
Tetsuma Ukai

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
Kohei Tatsumi

^aDepartment of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan
Akiya Ogawa

^bDepartment of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, Gakuen-cho 1-1, Nakaku, Sakai, Osaka 599-8531, Japan, Fax: +81(742)279289 Email: yamazaks@nara-edu.ac.jp

Abstract

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Abstract

The Lewis acid promoted reaction of 1,1-diarylallenes with ketone derivatives was examined. The tin(IV) chloride promoted reaction of diarylallenes with vinyl ketones gave indene derivatives through a conjugate addition/cyclization reaction. The reaction of diphenylallene with diethyl oxomalonate in the presence of one equivalent of tin(IV) chloride at –40 °C gave diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate as the major product through a carbonyl addition/cyclization reaction, whereas the same reactants in the presence of 0.2 equivalents of tin(IV) chloride at 80 °C gave diethyl (3-phenyl-1H-inden-2-yl)malonate. Diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate was also converted into the latter product on heating at 80 °C in the presence of 0.2 equivalents of tin(IV) chloride.

Key words

allenes - Lewis acids - ketones - cyclizations - Michael additions - addition reactions

Full Text

References

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Supplementary Material

Supporting Information (PDF)