Organocatalytic asymmetric one-pot sequential reaction: synthesis of highly substituted spirocyclohexanepyrazolones with six contiguous stereogenic carbons |
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Authors: | Ping Sun Chang-Yu Meng Feng Zhou Xin-Sheng Li Jian-Wu Xie |
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Affiliation: | 1. Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, PR China;2. Department of Chemistry and Materials, Yulin Normal University, Yulin 537000, PR China |
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Abstract: | An atom-economical synthesis of chiral polyfunctionalized spiropyrazolone derivatives based on the development of a new organocatalytic enantioselective one-pot sequential Michael/Michael/Aldol reaction of 1,3-dicarbonyl compounds with unsaturated pyrazolones and α,β-unsaturated aldehydes has been developed. The notable features of this one-pot sequential process include the generation of up to six consecutive stereogenic carbon centers including one quaternary stereocenter and five tertiary stereocenters with high enantioselectivities (up to 95% ee) and excellent diastereoselectivities (>99:1 d.r.). |
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