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Enantioselective Synthesis of Axially Chiral Anilides through Rhodium-Catalyzed [2+2+2] Cycloaddition of 1,6-Diynes with Trimethylsilylynamides
Abstract
We have developed a rhodium-catalyzed enantioselective intermolecular [2+2+2] cycloaddition of 1,6-diynes with trimethylsilylynamides for the synthesis of axially chiral anilides. The axial chirality is constructed at the formation of benzene rings with high enantioselectivity (up to 98% ee). It should be noted that the present reaction employs the readily prepared trimethylsilylynamides starting from commercially available bis(trimethysilyl)acetylene and the trimethylsilyl group of the product anilides is expected to be utilized for further functionalization.
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Cited by
Ynamides: A Modern Functional Group for the New Millennium
DeKorver, K. A., Li, H., Lohse, A. G., Hayashi, R., Lu, Z., Zhang, Y., & Hsung, R. P. (2010) · Chemical Reviews · doi:10.1021/cr100003s · Cited by 886
Ynamides: Versatile Tools in Organic Synthesis
Evano, G., Coste, A., & Jouvin, K. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200905817 · Cited by 812
Kumarasamy, E., Raghunathan, R., Sibi, M. P., & Sivaguru, J. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00136 · Cited by 756
Atropisomerism in Medicinal Chemistry: Challenges and Opportunities
Toenjes, S. T., & Gustafson, J. L. (2018) · Future Medicinal Chemistry · doi:10.4155/fmc-2017-0152 · Cited by 382
Metadata
- Authors
- Tanaka, K., Takeishi, K., & Noguchi, K.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-03-21
- Volume
- 128
- Issue
- 14
- Pages
- 4586-4587
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2163377997
- Cited by
- 247
- References
- 0
- FWCI
- 10.77
- Type
- journal article
- Language
- en
- Open access
- closed
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