4.8 Article

Asymmetric Construction of Functionalized Bicyclic Imides via [3+2] Annulation of MBH Carbonates Catalyzed by Dipeptide-Based Phosphines

Journal

ORGANIC LETTERS
Volume 14, Issue 14, Pages 3764-3767

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301647g

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Funding

  1. National University of Singapore [R-143-000-469-112]
  2. Singapore Peking Oxford Research Enterprise [COY-15-EWI-RCFSA/N197-1]
  3. GSK-EDB [R-143-000-491-592]

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A highly enantioselective [3 + 2] annulation of MBH carbonates and maleimides catalyzed by chiral phosphines has been developed. In the presence of 5 mol % of L-Thr-L-Val-derived phosphine 6, functionalized bicyclic imides were prepared in excellent yields, and with high diastereoselectivities and nearly perfect enantioselectivities.

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