4.6 Article

Synthesis of fully functionalised spiropyran pyrazolone skeletons via a formal [4+2] cascade process using β-nitro-styrene-derived MBH-alcohols

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RSC ADVANCES
卷 12, 期 53, 页码 34634-34638

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra06076k

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  1. DST-SERB [SB/FT/CS/079-2014]

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An efficient protocol was developed for the construction of spiro pyrazolone tetrahydropyran scaffolds at ambient temperature without the use of any metal catalyst. The reaction involved the formal [4 + 2] cyclisation of trans-beta-nitro-styrene-derived Morita-Baylis-Hillman alcohol with alpha-arylidene pyrazolone. The synthesis followed an oxa-Michael/Michael cascade pathway and yielded new C-C and C-O bonds. The use of quinine-derived catalyst resulted in high enantiomeric excess (ee) and excellent diastereoselectivity (>20:1).
An efficient protocol was established to construct spiro pyrazolone tetrahydropyran scaffolds at ambient temperature under metal-free conditions. The reaction proceeded via formal [4 + 2] cyclisation of trans-beta-nitro-styrene-derived Morita-Baylis-Hillman (MBH) alcohol with alpha-arylidene pyrazolone. The reaction followed an oxa-Michael/Michael cascade pathway, resulting in the formation of new C-C and C-O bonds. Organocatalytic synthesis of spiropyrazolones using quinine-derived catalyst resulted in 94% enantiomeric excess (ee) and excellent (>20 : 1) diastereoselectivity.

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