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Xu YW, Hu XP. Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides. Org Lett. 2019;21(19):8091-8096doi: 10.1021/acs.orglett.9b03081.
Xu, Y. W., & Hu, X. P. (2019). Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides. Organic letters, 21(19), 8091-8096. https://doi.org/10.1021/acs.orglett.9b03081
Xu, You-Wei, and Hu, Xiang-Ping. "Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides." Organic letters vol. 21,19 (2019): 8091-8096. doi: https://doi.org/10.1021/acs.orglett.9b03081
Xu YW, Hu XP. Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides. Org Lett. 2019 Oct 04;21(19):8091-8096. doi: 10.1021/acs.orglett.9b03081. Epub 2019 Sep 25. PMID: 31553196.
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Org Lett. 2019 Oct 04;21(19):8091-8096. doi: 10.1021/acs.orglett.9b03081. Epub 2019 Sep 25.

Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides.

Organic letters

You-Wei Xu, Xiang-Ping Hu

Affiliations

  1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023 , China.
  2. University of Chinese Academy of Sciences , Beijing 100049 , China.

PMID: 31553196 DOI: 10.1021/acs.orglett.9b03081

Abstract

A copper-catalyzed regio-, diastereo-, and enantioselective decarboxylative ring-opening [3 + 2] annulation of tertiary propargylic carbamates with γ-butenolides for the synthesis of optically active pyrrolidinones has been realized. The reaction proceeded through regioselective α-attack of γ-butenolide and generated highly congested vicinal tertiary and all-carbon quaternary stereocenters in pyrrolidinone scaffolds, featuring high stereoselective induction and broad functional group tolerance. Critical to the successful development of this method was the employment of copper catalysis in concert with a diPh-Pybox ligand.

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