Issue 81, 2016

Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones via a Michael-aldol sequential reaction

Abstract

An efficient organocatalytic method was developed for synthesizing functionalized spiropyrazolone derivatives containing four contiguous stereogenic centres by using a Michael-aldol consecutive reaction. We applied a quinine-derived squaramide catalyst to catalyze a reaction between 3-methyl-1-aryl-2-pyrazolin-5-ones and (E)-5-nitro-6-aryl-hex-5-en-2-ones, realizing the desired spiropyrazolones in moderate-to-good yields (up to 80%) with good-to-excellent stereoselectivities (up to >20 : 1 dr, 94% ee).

Graphical abstract: Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones via a Michael-aldol sequential reaction

Supplementary files

Article information

Article type
Communication
Submitted
29 ⵎⴰⵢ 2016
Accepted
25 ⵢⵓⵍ 2016
First published
16 ⵖⵓⵛ 2016

RSC Adv., 2016,6, 77474-77480

Organocatalytic one-pot asymmetric synthesis of functionalized spiropyrazolones via a Michael-aldol sequential reaction

M. Amireddy and K. Chen, RSC Adv., 2016, 6, 77474 DOI: 10.1039/C6RA13923J

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