4.6 Article

Non-metal Lewis acid-catalyzed cross-Claisen condensation for β-keto esters

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 42, Pages 9163-9166

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01785c

Keywords

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Funding

  1. NSFC [91956114]
  2. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
  3. Natural Science Foundation of Jiangsu Province [BK20210849]
  4. Innovation & Entrepreneurship Talents Plan of Jiangsu Province

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This work presents a new catalytic and highly chemoselective cross-Claisen condensation of esters, using silyl ketene acetals as carbonic nucleophiles. The process offers mild conditions and good functional group tolerance compared to traditional Claisen condensation.
In this work, we disclose a new catalytic and highly chemoselective cross-Claisen condensation of esters. In the presence of TBSNTf2 as a non-metal Lewis acid, various esters can undergo cross-Claisen condensation to form beta-keto esters which are important building blocks. Compared with the traditional Claisen condensation, this process, employing silyl ketene acetals (SKAs) as carbonic nucleophiles to achieve cross-Claisen condensation, requires mild conditions and has good tolerance of functional groups.

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