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Kashima K, Teraoka K, Uekusa H, et al. Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity. Org Lett. 2016;18(9):2170-3doi: 10.1021/acs.orglett.6b00791.
Kashima, K., Teraoka, K., Uekusa, H., Shibata, Y., & Tanaka, K. (2016). Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity. Organic letters, 18(9), 2170-3. https://doi.org/10.1021/acs.orglett.6b00791
Kashima, Kenichi, et al. "Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity." Organic letters vol. 18,9 (2016): 2170-3. doi: https://doi.org/10.1021/acs.orglett.6b00791
Kashima K, Teraoka K, Uekusa H, Shibata Y, Tanaka K. Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity. Org Lett. 2016 May 06;18(9):2170-3. doi: 10.1021/acs.orglett.6b00791. Epub 2016 Apr 13. PMID: 27074498.
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Org Lett. 2016 May 06;18(9):2170-3. doi: 10.1021/acs.orglett.6b00791. Epub 2016 Apr 13.

Rhodium-Catalyzed Atroposelective [2 + 2 + 2] Cycloaddition of Ortho-Substituted Phenyl Diynes with Nitriles: Effect of Ortho Substituents on Regio- and Enantioselectivity.

Organic letters

Kenichi Kashima, Kota Teraoka, Hidehiro Uekusa, Yu Shibata, Ken Tanaka

Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology , Koganei, Tokyo 184-8588, Japan.

PMID: 27074498 DOI: 10.1021/acs.orglett.6b00791

Abstract

Axially chiral 3-(2-halophenyl)pyridines were successfully synthesized in high yields with excellent enantioselectivity by the cationic rhodium(I)/(S)-H8-BINAP complex-catalyzed atroposelective [2 + 2 + 2] cycloaddition of (o-halophenyl)diynes with nitriles. Interestingly, regio- and enantioselectivity highly depend on ortho substituents on the phenyl group of diynes. When the ortho substituents were methoxy and methoxycarbonyl groups, axially chiral 3-arylpyridines were obtained as a major product, while enantioselectivity was lowered significantly. On the other hand, when the ortho substituents were alkyl groups, regioselectivity was switched to give achiral 6-arylpyridines in high yields.

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