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Wang Z, Xu H, Su Q, et al. Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. Org Lett. 2017;19(12):3111-3114doi: 10.1021/acs.orglett.7b01221.
Wang, Z., Xu, H., Su, Q., Hu, P., Shao, P. L., He, Y., & Lu, Y. (2017). Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. Organic letters, 19(12), 3111-3114. https://doi.org/10.1021/acs.orglett.7b01221
Wang, Zhen, et al. "Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations." Organic letters vol. 19,12 (2017): 3111-3114. doi: https://doi.org/10.1021/acs.orglett.7b01221
Wang Z, Xu H, Su Q, Hu P, Shao PL, He Y, Lu Y. Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations. Org Lett. 2017 Jun 16;19(12):3111-3114. doi: 10.1021/acs.orglett.7b01221. Epub 2017 May 31. PMID: 28560873.
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Org Lett. 2017 Jun 16;19(12):3111-3114. doi: 10.1021/acs.orglett.7b01221. Epub 2017 May 31.

Enantioselective Synthesis of Tetrahydropyridines/Piperidines via Stepwise [4 + 2]/[2 + 2] Cyclizations.

Organic letters

Zhen Wang, Huacheng Xu, Qin Su, Ping Hu, Pan-Lin Shao, Yun He, Yixin Lu

Affiliations

  1. School of Pharmaceutical Sciences and Innovative Drug Research Centre, Chongqing University , Chongqing 401331, P.R. China.
  2. Department of Chemistry, National University of Singapore , Singapore 117543, Singapore.
  3. National University of Singapore (Suzhou) Research Institute , Suzhou 215123, P.R. China.

PMID: 28560873 DOI: 10.1021/acs.orglett.7b01221

Abstract

A phosphine-catalyzed novel enantioselective [4 + 2]-annulation reaction between allene ketones and 1-azadienes has been developed, and tetrahydropyridines were obtained in good yields and with excellent enantioselectivities. Subsequent exposure of tetrahydropyridines to benzyne leads to a [2 + 2]-cyclization, creating optically enriched polycyclic piperidines with a quaternary stereogenic center and a cyclobutene moiety. The reported stepwise [4 + 2]/[2 + 2]-cycloadditions represent a new approach to access enantiomerically enriched nitrogen-containing six-membered ring systems.

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