Synfacts 2008(3): 0268-0268  
DOI: 10.1055/s-2008-1042687
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Diels-Alder Reaction in Ionic Liquids: Remarkable Reactivity and Selectivity

Contributor(s):Hisashi Yamamoto, Matthew B. Boxer
C.-E. Yeom, H. W. Kim, Y. J. Shin, B. M. Kim*
Seoul National University, Republic of Korea
Chiral Bis(oxazoline)-Copper Complex Catalyzed Diels-Alder Reaction in Ionic Liquids: Remarkable Reactivity and Selectivity Enhancement, and Efficient Recycling of the Catalyst
Tetrahedron Lett.  2007,  48:  9035-9039  
Further Information

Publication History

Publication Date:
21 February 2008 (online)


Significance

The authors report a highly endo-selective Diels-Alder reaction in ionic liquids. The reaction proceeds with high enantioselectivity even with a low (0.6 mol%) catalyst loading. The catalyst can be recycled up to 18 times without serious deterioration of selectivity or reactivity.

Comment

With the importance of ionic liquids emerging over the past decade, this is an interesting report in this area. While the Diels-Alder reaction is widely studied, this is a nice report from the standpoint that the catalyst system is very effective and can be recycled.