Journal of Organic Chemistry p. 2148 - 2152 (1981)
Update date:2022-08-05
Topics:
Shvo, Youval
Kaufman, Edward D.
The stereoselectivity of the oxidation of N-alkylpiperidines was studied with the aid of the conformationally biassing 4-tert-butyl substituent.The stereoselectivity was always >95percent and showed little sensitivity to the nature of the N-alkyl substituent.The axial approach was found to be predominating stereochemical oxidation path.A brief study of the effects of solvent, temperature, and oxidant on the stereoselectivity was made.The 1,4-dimethylpiperazine system was investigated, and its oxidation at room temperature resulted in 100percent of trans-1,4-dimethylpiperazine 1,4-dioxide.A method to modulate the stereoselectivity in the formation of saturated heterocyclic amine oxides was developed by inverting the sequence of introduction of the nitrogen substituents.With cis-8-methyl-8-azabicyclo<4.3.0>nonane oxidation is preferred from that side of the molecule which is sterically more hindered.
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Doi:10.1016/j.bmc.2004.07.034
(2004)Doi:10.1515/znb-1980-1130
(1980)Doi:10.1021/jo00324a017
(1981)Doi:10.1016/S0040-4039(00)93692-X
(1980)Doi:10.1016/0022-1902(81)80242-4
(1981)Doi:10.1007/BF00944221
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