4.8 Article

Dynamic Kinetic Asymmetric [3+2] Annulation Reactions of Aminocyclopropanes

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 17, 页码 6239-6242

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AMER CHEMICAL SOC
DOI: 10.1021/ja5024578

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  1. F. Hoffmann-La Roche Ltd.
  2. Swiss National Science Foundation (SNSF) [200021_129874, 200020_149494]
  3. Swiss National Science Foundation (SNF) [200020_149494, 200021_129874] Funding Source: Swiss National Science Foundation (SNF)

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We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.

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