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Honma M, Sawada T, Fujisawa Y, et al. Asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones. J Am Chem Soc. 2003;125(10):2860-1doi: 10.1021/ja029534l.
Honma, M., Sawada, T., Fujisawa, Y., Utsugi, M., Watanabe, H., Umino, A., Matsumura, T., Hagihara, T., Takano, M., & Nakada, M. (2003). Asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones. Journal of the American Chemical Society, 125(10), 2860-1. https://doi.org/10.1021/ja029534l
Honma, Masahiro, et al. "Asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones." Journal of the American Chemical Society vol. 125,10 (2003): 2860-1. doi: https://doi.org/10.1021/ja029534l
Honma M, Sawada T, Fujisawa Y, Utsugi M, Watanabe H, Umino A, Matsumura T, Hagihara T, Takano M, Nakada M. Asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones. J Am Chem Soc. 2003 Mar 12;125(10):2860-1. doi: 10.1021/ja029534l. PMID: 12617637.
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J Am Chem Soc. 2003 Mar 12;125(10):2860-1. doi: 10.1021/ja029534l.

Asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones.

Journal of the American Chemical Society

Masahiro Honma, Takashi Sawada, Yuri Fujisawa, Masayuki Utsugi, Hideaki Watanabe, Akinori Umino, Takehiko Matsumura, Takayuki Hagihara, Masashi Takano, Masahisa Nakada

Affiliations

  1. Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.

PMID: 12617637 DOI: 10.1021/ja029534l

Abstract

This work describes the development of a highly enantioselective asymmetric catalysis on the intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones. We have found that the catalytic asymmetric intramolecular reactions of alpha-diazo-beta-keto sulfones generally proceed with high enantioselectivity when the alpha-diazo-beta-keto mesityl sulfone is used with the newly prepared ligand 2e. The absolute configuration of products has been determined by X-ray crystallographic analysis, and the outcome of the enantioselectivities is explained well by our proposed models A and B. The products possess great potential for natural product synthesis because (1) many different chemistries of cyclopropane, ketone, and sulfone are available, and (2) the products are generally highly crystalline, facilitating the supplies of enantiomerically pure synthetic intermediates.

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