4.8 Article

Squaramide-Tertiary Amine Catalyzed Asymmetric Cascade Sulfa-Michael/Michael Addition via Dynamic Kinetic Resolution: Access to Highly Functionalized Chromans with Three Contiguous Stereocenters

Journal

ORGANIC LETTERS
Volume 15, Issue 6, Pages 1190-1193

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol400025a

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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 asymmetric cascade sulfa-Michael/Michael addition reaction catalyzed by a chiral bifunctional squaramide-tertiary amine catalyst has been developed. This organocatalytic cascade reaction provides easy access to highly functionalized chromans with three contiguous stereocenters, including one quaternary center. In addition, a novel cascade sulfa Michael/retro-sulfa-Michael/sulfa-Michael/Michael reaction process, Involving dynamic kinetic resolution, is described.

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