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

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

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

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For mechanistic considerations, see:

<A NAME="RA57910ST-67A">67a</A> Yu Z.-X. Wender PA. Houk KN. J. Am. Chem. Soc.  2004,  126:  9154 

<A NAME="RA57910ST-67B">67b</A> Yu Z.-X. Cheong PH.-Y. Liu P. Legault CY. Wender PA. Houk KN. J. Am. Chem. Soc.  2008,  130:  2378 

<A NAME="RA57910ST-67C">67c</A> Liu P. Cheong PH.-Y. Yu Z.-X. Wender PA. Houk KN. Angew. Chem. Int. Ed.  2008,  47:  3939 

<A NAME="RA57910ST-68A">68a</A> Owada Y. Matsuo T. Iwasawa N. Tetrahedron  1997,  53:  11069 

<A NAME="RA57910ST-68B">68b</A> Hayashi M. Ohmatsu T. Meng Y.-P. Saigo K. Angew. Chem. Int. Ed.  1998,  37:  837 

<A NAME="RA57910ST-68C">68c</A> Murakami M. Itami K. Ubukata M. Tsuji I. Ito Y. J. Org. Chem.  1998,  63:  4 

<A NAME="RA57910ST-68D">68d</A> Schmittel M. Mahajan AA. Bucher G. Bats JW. J. Org. Chem.  2007,  72:  2166 

<A NAME="RA57910ST-68E">68e</A> Hiroi K. Kato F. Oguchi T. Saito S. Sone T. Tetrahedron Lett.  2008,  49:  3567 

<A NAME="RA57910ST-69">69</A>

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.