AI Article Synopsis
- The study introduces the first investigation of nitrogen-nitrogen double bonds in chiral phosphine catalysis, focusing on their role in asymmetric reactions.
- The researchers successfully developed a phosphine-catalyzed [3+2] cycloaddition using diazenes and Morita-Baylis-Hillman carbonates to produce chiral dihydropyrazoles.
- The reactions were carried out under mild conditions, yielding high product yields and excellent enantioselectivities with various combinations of MBH carbonates and diazenes.
Article Abstract
Although carbon-carbon, carbon-nitrogen, and carbon-oxygen double bonds or their combinations have extensively been applied in phosphine-catalyzed asymmetric cycloaddition, a nitrogen-nitrogen double bond has never been investigated in chiral phosphine catalysis. In this paper, we present phosphine-catalyzed asymmetric [3+2] cycloaddition of diazenes with Morita-Baylis-Hillman (MBH) carbonates to give chiral dihydropyrazoles in high yields with excellent enantioselectivities. Various MBH carbonates and diazenes worked well under the mild reaction conditions.
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| http://dx.doi.org/10.1021/acs.orglett.9b02800 | DOI Listing |
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