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Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition

of 5H-thiazole-4-ones with N-itaconimides

Shuai Qiu, Choon-Hong Tan and Zhiyong Jiang

Beilstein J. Org. Chem., 2016, 12, 2293 - 2297

Abstract: A dipeptide-based urea-amide tertiary amine (DP-UAA) was shown to be an effective Brønsted base catalyst for the first asymmetric annulation reaction between 5H-thiazol-4-ones and N-itaconimides. High levels of enantioselectivity (up to 99% ee) and diastereoselectivity (>19:1 dr) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides.

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