Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides

Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides

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 fo...

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Bibliographic Details
Main Authors: Shuai Qiu, Choon-Hong Tan, Zhiyong Jiang
Format: Article
Language:English
Published: Beilstein-Institut 2016-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
[4 + 2] annulation
asymmetric organocatalysis
dipeptide-based Brønsted bases
5H-thiazol-4-ones
N-itaconimides
Online Access:https://doi.org/10.3762/bjoc.12.222
Description
Summary: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.
ISSN:1860-5397

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