AI Article Synopsis
- A new method has been developed using squaramide as a catalyst for a domino reaction involving -Boc ketimines and γ-hydroxyenones to create spirooxazolidines.
- The most effective catalyst was a hydroquinine-derived bifunctional squaramide, enabling the construction of complex molecules with two stereocenters.
- This approach yields products with good amounts of both diastereoselectivity and enantioselectivity, and it can be scaled up for larger reactions.
Article Abstract
A squaramide-catalyzed asymmetric ,-acetalization/aza Michael addition domino reaction between -Boc ketimines derived from pyrazolin-5-ones and γ-hydroxyenones has been developed for the construction of pyrazolinone embedded spirooxazolidines. A hydroquinine derived bifunctional squaramide catalyst was found to be the most effective for this cascade spiroannulation. This new protocol allows the generation of two stereocenters and the desired products are obtained in good yields with moderate to good diastereoselectivities (up to 3.3 : 1 dr) and high enantioselectivities (up to >99% ee) from a range of substituted -Boc pyrazolinone ketimines and γ-hydroxyenones. The developed protocol is amenable for a scale-up reaction.
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| http://dx.doi.org/10.1039/d2ob02290g | DOI Listing |
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