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Synfacts 2006(10): 1029-1029  
DOI: 10.1055/s-2006-949285
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Tetra-ortho-substituted Axially Chiral Biaryls via [2+2+2] Cycloadditions

Contributor(s): Mark Lautens, Frédéric Ménard
G. Nishida, N. Suzuki, K. Noguchi, K. Tanaka*
Tokyo University of Agriculture and Technology, Japan
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Publikationsdatum:
21. September 2006 (online)

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Significance

Complex axially chiral biaryls can be prepared in one step from two acyclic starting materials. Besides this method, very few methods allow the preparation of tetra-ortho-substituted biaryl compounds. With the double [2+2+2] cyclo­addition, in most cases the mono-annulated products 7 are observed and can be resubjected to a second cycloaddition to obtain non-symmetrically substituted biaryl compounds 8 with high enan­tioselectivity.