Elsevier

Tetrahedron Letters

Volume 46, Issue 7, 14 February 2005, Pages 1103-1105
Tetrahedron Letters

Improved synthesis of 2,2′-dimethoxy-1,1′-binaphthyl-3,3′-diacetic acid derivatives

https://doi.org/10.1016/j.tetlet.2004.12.095Get rights and content

Abstract

During the past decade, the chemistry of BINAP, BINAM, and BINOL derivatives experienced an important development due to multiple applications in catalysis, metallo-supramolecular chemistry and material science. Consequently, the need to develop functionalized binaphthyl derivatives became crucial. In this context, we were interested in preparing 2,2′-dimethoxy-1,1′-binaphthyl-3,3′-diacetic acid species. The latter were efficiently prepared using a modified Arndt–Eistert reaction that afforded the expected chiral diacid in good yield. Compared to the method we described earlier, this new strategy allows the preparation of the target homologated diacid chloride in a very efficient manner, limiting wastes and tedious column chromatographies.

Graphical abstract

An optimized and straightforward synthesis of a key, chiral dicarboxylic acid building block is described.

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Acknowledgements

The authors would like to acknowledge the CNRS for financial support.

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