4.7 Article

Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: enantioselective construction of functionalized spirooxindole tetrahydroquinolines

Journal

CHEMICAL COMMUNICATIONS
Volume 49, Issue 78, Pages 8842-8844

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3cc44930k

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Funding

  1. National Natural Science Foundation of China [21272024]
  2. Science and Technology Innovation Program of Beijing Institute of Technology [2011CX01008]
  3. Development Program for Distinguished Young and Middle-aged Teachers of Beijing Institute of Technology

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An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee).

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