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6-exo-Amino-3-azabicyclo[3,1,0]hexane is an essential fragment of the broad-spectrum antibiotic Trovafloxacin,see; Brighty, K. E. WO Patent 91/02526, 1991; EU Patent 413455, 1991; Chem. Abstr. 1991, 115, 232216; U.S. Patent 5, 164.402, 1992; Chem. Abstr. 1993, 119, 117227. Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097.
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6-exo-Amino-3-azabicyclo[3,1,0]hexane is an essential fragment of the broad-spectrum antibiotic Trovafloxacin,see; Brighty, K. E. WO Patent 91/02526, 1991; EU Patent 413455, 1991; Chem. Abstr. 1991, 115, 232216; U.S. Patent 5, 164.402, 1992; Chem. Abstr. 1993, 119, 117227. Brighty, K. E.; Castaldi, M. J. Synlett 1996, 1097.
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This now readily available diacetate 3 can serve as a precursor for the interesting, yet little studied 2,3-diethenyl-1,3-butadiene, see; Bailey, W. J.; Nielsen, N. A. J. Org. Chem. 1962, 27, 3088. Buchan, C. M.; Cadogan, J. I. G.; Gosney, I.; Henry, W. J. J. Chem. Soc., Chem. Commun. 1985, 24, 1785. Brain, P. T.; Smart, B. A.; Robertson, H. E.; Davis, M. J.; Rankin, D. W. H.; Henry, W. J.; Gosney, I. J. Org. Chem. 1997, 62, 2767.
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This now readily available diacetate 3 can serve as a precursor for the interesting, yet little studied 2,3-diethenyl-1,3-butadiene, see; Bailey, W. J.; Nielsen, N. A. J. Org. Chem. 1962, 27, 3088. Buchan, C. M.; Cadogan, J. I. G.; Gosney, I.; Henry, W. J. J. Chem. Soc., Chem. Commun. 1985, 24, 1785. Brain, P. T.; Smart, B. A.; Robertson, H. E.; Davis, M. J.; Rankin, D. W. H.; Henry, W. J.; Gosney, I. J. Org. Chem. 1997, 62, 2767.
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a) This type of carbometallation across the double bond of 2,5-dihydrofuran with subsequent ring opening has been observed with zirconocene complexes of strained cyclic alkynes, and with alkylmagnesium halides under zirconocene catalysis, respectively, see; Cuny, G. D.; Buchwald, S. L. Organometallics 1991, 10, 363.
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N-Phenyl-2,5-dihydropyrrol, just like the N-benzyl derivative [refs. (4,5b)], in the presence of N,N-dibenzylformamide gave the corresponding 5-(dibenzylamino)-3-phenyl-3-azabicyclo[3,1,0]hexane. Langer, R.; Williams, C. M.; de Meijere, A.; unpublished results.
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Formation of σ-allyltitanium complexes from allyl phenyl ether has previously been observed, see; ref. (8)
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Formation of σ-allyltitanium complexes from allyl phenyl ether has previously been observed, see; ref. (8).
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