Construction of the (1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane Ring System

Diastereoselective Syntheses of N-Protected Derivatives of 1α,5α,6β-6-Amino-3-azabicyclo[3.1.0]hexane; A Route to Trovafloxacin 6β-Diastereomer

“…Treatment of 7 with one equivalent of hydrogen in methanol and a palladium charcoal catalyst led to a mixture of debenzylated products 11-14. The missing selectivity in the hydrogenolytic debenzylation of 7 with respect to the analogous reaction of carbonitrile 8 should be the consequence of the absence of a deactivating group at C (6) in the case of diamine 7 (Scheme 2).…”

“…The 6-amino moiety at the cyclopropane system, thereby, is generated by a Curtius degradation 1,4,5 or the reduction of the nitro moiety. 6 Predominantly or exclusively 6a-isomers were obtained in all sequences. On the other hand, amino-chloroenamines of type 6 proved to be simple starting materials for the synthesis of 6-amino-3-azabicyclo[3.1.0]hexane derivatives [7][8][9][10][11][12][13][14][15] leading mostly to 6b-isomers.…”

“…6a-Amine 1a was synthesized as Boc-protected compound 1b via carboxylic acid 3 1,4,5 or nitro derivative 4 6 both by multistep procedures. The 6-amino moiety at the cyclopropane system, thereby, is generated by a Curtius degradation 1,4,5 or the reduction of the nitro moiety.…”

Complementary Ways to Diastereomers of Bridged Aminopiperidine Derivatives - A Stereochemical Challenge

“…9). Cyclopropanation of a pyrroline compound 81 or 82 by a C 1 -unit (bromonitromethane, base and 81 [85,86], ethyl diazoacetate and 81 [87] or 82/ rhodium acetate [87,88], dibenzylformamide, titanium inside-attack outside-attack tetraisopropoxide, isopropylmagnesium bromide and 82 [89]) or aza-annulation of derivatives of type 83 [90,91] served as access to the azabicyclohexane skeleton.…”

Quinolone Antibacterials

“…Pyrrolidine derivatives bridged by three-membered rings may be obtained from benzylmaleimide by addition of bromonitromethane and subse-o t) (BRAISH 1992;BRAISH et al 1996). The various synthesis methods are correspondingly diverse.…”