4.7 Article

Multi-component syntheses of 2-pyrrolines and organocatalytic asymmetric syntheses of functionalized chiral 2-pyrrolines

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 4, Pages -

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01267j

Keywords

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Funding

  1. Scientific Research Start-up Funds for Openly-recruited Doctors, Science and Technology Innovation Funds of Gansu Agricultural University, China [GAU-KYQD-2018-12, GAU-KYQD-2018-19]
  2. National Natural Science Foundation of China [32060486]
  3. Developmental Funds of Innovation Capacity in Higher Education of Gansu, China [2019A-054, 2019A-052]
  4. Gansu Provincial Key Laboratory of Aridland Crop Science, Gansu Agricultural University, China [GSCS-2020-5, GSCS-2019-8]

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The green and atom-economical synthesis of functionalized 2-pyrrolines with two contiguous stereocenters was achieved using a catalytic amount of bifunctional chiral squaramide in a one-pot annulation reaction, providing good yields under mild conditions.
The green and atom-economical synthesis of functionalized 2-pyrrolines has been achieved by carrying out the multi-component tandem [2 + 2 + 1] annulation reaction of simple and commercially available starting materials, namely, an aldehyde, glycine ester hydrochloride, and benzoylacetonitrile. In the presence of a catalytic amount of bifunctional chiral squaramide, the sequential one-pot annulation reaction provided a highly stereoselective way to construct fully substituted 2-pyrrolines containing two contiguous stereocenters, from imino esters with benzoylacetonitriles in good yields under mild conditions.

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