Lewis acid mediated nucleophilic ring opening followed by cycloaddition of 2-aryl-N-tosylaziridines with carbonyl compounds: further support towards an SN2-type mechanism |
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| Authors: | Manas K Ghorai Koena Ghosh |
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| Institution: | Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India |
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| Abstract: | A highly regioselective SN2-type ring opening of 2-aryl-N-tosylaziridines with carbonyl compounds in the presence of a Lewis acid to afford various 1,3-oxazolidines and 1,2-amino alcohols in excellent yields and moderate to high enantioselectivity is described. The formation of non-racemic products provides convincing evidence for the SN2-type ring opening mechanism. |
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| Keywords: | 2-Aryl-N-tosylaziridine Cu(OTf)2 Zn(OTf)2 BF3· OEt2 Nucleophilic ring opening SN2 pathway Mechanism Carbonyl 1 3-Oxazolidine 1 2-Amino alcohol |
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