Phosphinoyl-aziridines as a new class of chiral catalysts for enantioselective Michael addition |
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Authors: | Zuzanna Wujkowska Anna Zawisza Stanis?aw Le?niak Micha? Rachwalski |
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Institution: | Department of Organic and Applied Chemistry, University of ?ód?, Tamka 12, 91-403 ?ód?, Poland |
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Abstract: | A series of new optically pure phosphine oxides containing chiral aziridine subunit were synthesized in good yields and applied as organocatalysts in asymmetric Michael reaction of various aliphatic aldehydes with β-nitrostyrene. The corresponding organocatalysts were synthesized starting from optically pure aziridines in a few simple efficient steps. The appropriate Michael adducts were obtained in most cases in very high chemical yield (up to 97%), excellent enantioselectivity (up to 98% of ee) and diastereoselectivity (up to 95:5 of dr). |
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Keywords: | Asymmetric synthesis Aziridines Chiral catalysts Michael addition Organocatalysis |
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