Enantioselective synthesis of dialkylated N-heterocycles by palladium-catalyzed allylic alkylation

  1. Numajiri, Y. 3
  2. Jiménez-Osés, G. 2
  3. Wang, B. 1
  4. Houk, K.N. 2
  5. Stoltz, B.M. 3
  1. 1 BioTools, Inc., 17546 Bee Line Highway, Jupiter, FL, United States
  2. 2 University of California Los Angeles
    info

    University of California Los Angeles

    Los Ángeles, Estados Unidos

    ROR https://ror.org/046rm7j60

  3. 3 California Institute of Technology
    info

    California Institute of Technology

    Pasadena, Estados Unidos

    ROR https://ror.org/05dxps055

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Revista:
Organic Letters

ISSN: 1523-7060

Any de publicació: 2015

Volum: 17

Número: 5

Pàgines: 1082-1085

Tipus: Article

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DOI: 10.1021/OL503425T SCOPUS: 2-s2.0-84924258547 WoS: WOS:000350841300006 GOOGLE SCHOLAR

Altres publicacions en: Organic Letters

Resum

The enantioselective synthesis of α-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted α-positions. Broad functional group tolerance was explored at the α-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds. © 2015 American Chemical Society.