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Synthesis of 4,4-disubstituted -lactams by regiospecific electrophile- and silver-induced ring expansion of 2,2-disubstituted 1-methoxycyclopropylamines
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| Abstract |
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| 2,2-Disubstituted 1-methoxycyclopropylamines underwent regiospecific ring expansion to 1,4,4-trisubstituted 2-azetidinones by N-chlorination with tert-butyl hypochlorite and subsequent rearrangement with silver tetrafluoroborate. Upon thermolysis, 4,4-disubstituted beta-lactams suffer a characteristic ring opening to afford beta,gamma-unsaturated carboxylic amides. The reduction of 1,4,4-trisubstituted 2-azetidinones with lithium aluminum hydride afforded 1,2,2-trisubstituted azetidines. | | |
| Language |
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English
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| Source (journal) |
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The journal of organic chemistry. - Washington, D.C. | |
| Publication |
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Washington, D.C. : 1996
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0022-3263
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| Volume/pages |
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61:19(1996), p. 6500-6503
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A1996VJ00600013
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