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Zhang S, Li L, Hu Y, et al. Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Org Lett. 2015;17(20):5036-9doi: 10.1021/acs.orglett.5b02514.
Zhang, S., Li, L., Hu, Y., Li, Y., Yang, Y., Zha, Z., & Wang, Z. (2015). Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Organic letters, 17(20), 5036-9. https://doi.org/10.1021/acs.orglett.5b02514
Zhang, Sheng, et al. "Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones." Organic letters vol. 17,20 (2015): 5036-9. doi: https://doi.org/10.1021/acs.orglett.5b02514
Zhang S, Li L, Hu Y, Li Y, Yang Y, Zha Z, Wang Z. Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones. Org Lett. 2015 Oct 16;17(20):5036-9. doi: 10.1021/acs.orglett.5b02514. Epub 2015 Sep 28. PMID: 26414655.
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Org Lett. 2015 Oct 16;17(20):5036-9. doi: 10.1021/acs.orglett.5b02514. Epub 2015 Sep 28.

Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones.

Organic letters

Sheng Zhang, Lijun Li, Yanbin Hu, Yanan Li, Yu Yang, Zhenggen Zha, Zhiyong Wang

Affiliations

  1. Hefei National Laboratory for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology, Department of Chemistry, University of Science and Technology of China , Hefei, Anhui 230026, China.

PMID: 26414655 DOI: 10.1021/acs.orglett.5b02514

Abstract

A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active β-amino ketones were directly obtained. More importantly, two different intermediates involved in the reaction were detected and identified by (19)F NMR and HRMS analysis. Furthermore, the synthetic utility of the products was demonstrated by the synthesis of the biologically active fluoroalkyl β-amino alcohols.

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