Organocatalytic Asymmetric Synthesis of α‑Oxetanyl and α‑Azetidinyl Tertiary Alkyl Fluorides and Chlorides
journal contributionposted on 23.01.2018, 19:53 by Ransheng Ding, Christian Wolf
Asymmetric thiourea and squaramide catalysis provides access to synthetically versatile α-oxetanyl and α-azetidinyl alkyl halides exhibiting a tetrasubstituted chiral carbon center with high yields and enantioselectivities. The products are readily transformed with negligible erosion of enantiopurity and excellent diastereoselectivity to a diverse group of multifunctional compounds including fluorooxindoles with two contiguous chirality centers, fluorinated heterocyclic spiranes, and polyspiro compounds.
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α- azetidinyl alkyl halidestetrasubstituted chiral carbon centerAzetidinyldiastereoselectivityfluorooxindoleChlorides Asymmetric thioureachirality centersα- oxetanylsyntheticallyaccessAlkylenantiopurityOrganocatalytic Asymmetric Synthesiserosionpolyspiro compoundsmultifunctional compoundsFluorideheterocyclic spiranesyieldOxetanylsquaramide catalysisenantioselectivitieTertiary