4.8 Article

Copper-Catalyzed Enantioselective Allylboration of Alkynes: Synthesis of Highly Versatile Multifunctional Building Blocks

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 50, Pages 18230-18234

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910707

Keywords

asymmetric catalysis; boron; copper; diversity-oriented synthesis; multicomponent reactions

Funding

  1. AEI [RYC-2012-11749, CTQ2017-88451-R]
  2. Xunta de Galicia [ED431F 2016/006, GRC2014/032, ED431C 2018/04]
  3. Xunta de Galicia (Centro singular de investigacion de Galicia accreditation 2016-2019) [ED431G/09]
  4. European Union (ERDF)

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The first copper-catalyzed enantioselective allylboration of alkynes is reported. The method employs a multitasking chiral NHC-Cu catalyst and provides access to densely functionalized molecules from simple starting materials with excellent levels of chemo-, regio-, and enantioselectivity. These multifunctional products display highly versatile reactivity as shown by the synthesis of a variety of non-racemic molecular scaffolds. DFT calculations were conducted to gain insight into the high selectivity levels of this catalytic process.

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