Chiral bicyclic guanidines: a concise and efficient aziridine-based synthesis |
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Authors: | Weiping Ye |
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Institution: | Department of Chemistry, 3 Science Drive 3, National University of Singapore, Singapore 117543, Singapore |
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Abstract: | A series of chiral bicyclic guanidines, either symmetrical or non-symmetrical, was synthesized using a concise and efficient aziridine-based synthetic methodology. Starting from commercial amino alcohols, five synthetic steps were performed, with only three requiring chromatographic purification, giving the desired guanidines in 43-71% overall yield. Preliminary studies using these guanidines showed moderate enantioselectivity for several Michael reactions. |
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Keywords: | Guanidine Aziridine Michael reaction Enantioselectivity Regioselectivity |
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