4.7 Article

exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP

Journal

CHEMICAL COMMUNICATIONS
Volume 49, Issue 83, Pages 9642-9644

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc45493b

Keywords

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Funding

  1. 973 program [2011CB808600]
  2. NSFC [20972117, 21172176]
  3. Fundamental Research Funds for the Central Universities
  4. [NCET-10-0649]
  5. [IRT1030]

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An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with alpha-methylene-gamma-butyrolactone, which exhibited high diastereoselectivity (>98:2), excellent enantioselectivity (96->99% ee) and a broad substrate scope under mild conditions.

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