Copper‐Catalyzed Enantioselective Allylboration of Alkynes: Synthesis of Highly Versatile Multifunctional Building Blocks
Eva Rivera‐Chao, Maider Mitxelena, Jesús A. Varela, Martín Fañanás‐Mastral
Angewandte Chemie International Edition · 2019 · 10.1002/anie.201910707
Abstract
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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The authors reported (Inductive Diastereoselective Rationale for a Catalytic Strategy to Build Densely Chiral Five-Membered Carbocycles) the application of Fananas-Mastral and co-worker's methodology to synthesise enantioenriched borylated 1,4-dienes in a single step, as starting points for their own five-membered carbocycle targets, including the resynthesis of compounds 18, 19 and 24 from the original paper alongside previously unreported analogues. All three compounds were resynthesised with almost identical enantiomeric ratios (±0.5 difference) and slightly lower yields (37% lower for 18, 6% lower for 19, 26% lower for 24). The scale of these reactions was not disclosed.
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