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Synfacts 2006(7): 0681-0681  
DOI: 10.1055/s-2006-941866
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Axially Chiral Aromatic Amides via [2+2+2] Cycloaddition

Contributor(s): Mark Lautens, Andrew Martins
K. Tanaka*, K. Takeishi, K. Noguchi
Tokyo University of Agriculture and Technology, Japan
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Publication History

Publication Date:
22 June 2006 (online)

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Significance

In the presence of a rhodium(I)/(S)-xyl-BINAP catalyst system, 1,6-diynes and tri­methylsilylynamides undergo a [2+2+2] cycloaddition to generate hexasubstituted aromatic, axially chiral amides. The enantioselectivities range from good to excellent, and the yields range from poor to good, although significant quantities of starting trimethylsilylynamide can be recovered chromatographically. The main side reaction is the homotrimerization of the 1,6-diyne, which accounts for some of the low yields observed.