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Synlett 2011(5): 594-614  
DOI: 10.1055/s-0030-1259693
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Construction of Diverse Ring Systems Based on Allene-Multiple Bond Cycloaddition

Fuyuhiko Inagaki, Shinji Kitagaki, Chisato Mukai*
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
Fax: +81(76)2344410; e-Mail: cmukai@kenroku.kanazawa-u.ac.jp;
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Publication History

Received 10 November 2010
Publication Date:
25 February 2011 (online)

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Abstract

Cycloaddition and cycloisomerization based on the interaction between an allene and another multiple bond, such as an alkyne, alkene, or additional allene, enabled us to build a variety of useful cyclic structures. This account describes our research on allene cycloaddition and cycloisomerization, categorizing the reactions by the proper reaction mode and the cyclic framework of the product.

1 Introduction

2 Construction of Bicyclo[m.3.0] Skeletons via Carbonylative [2+2+1] Cycloaddition

2.1 From Allene-Ynes and Aza Analogues

2.2 From Allene-Enes

2.3 From Bis-allenes

3 Construction of Bicyclo[m.2.0] Skeletons via [2+2] Cyclo­addition

3.1 From Allene-Ynes

3.2 From Bis-allenes

4 Construction of Bicyclo[4.4.0] Skeletons via 6π-Electrocyclization/[4+2] Cycloaddition

5 Construction of Monocyclic Polyenes via Cycloisomerization

5.1 From Allene-Ynes

5.2 From Allene-Enes

5.3 From Bis-allenes

6 Construction of Bicyclo[5.m.0] Skeletons via [5+2] Cyclo­addition

7 Conclusions and Outlook

Key words

allenes - cycloadditions - Pauson-Khand-type reactions - cycloisomerizations - medium-sized rings

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A successful example of a [RhCl(CO)2]2-catalyzed [5+2] cycloaddition involving terminal alkyne and (E)-2-(1-ethoxycyclopropyl)vinyl moieties was reported: See ref. 65g.