A short and efficient synthesis of enantiopure (+)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one utilizing an asymmetric desymmetrization protocol: formal total synthesis of (-)-epibatidine

Pandey, Ganesh ; Tiwaria, Shashi Kant ; Singh, Ram Shanker ; Mali, Raghao S. (2001) A short and efficient synthesis of enantiopure (+)-N-Boc-7-azabicyclo[2.2.1]heptan-2-one utilizing an asymmetric desymmetrization protocol: formal total synthesis of (-)-epibatidine Tetrahedron Letters, 42 (23). pp. 3947-3949. ISSN 0040-4039

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4039(01)00616-5

Abstract

A short and efficient synthesis of optically pure (+)-N-Boc-azabicyclo[2.2.1]hept-2-one (2), a precursor in the synthesis of natural (-)-epibatidine (1), is reported by the asymmetric desymmetrization of meso-N-methoxycarbonyl-2,3-bis(phenylsulfonyl)-7-azabicyclo[2.2.1]hept-2-ene (3).

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Asymmetric Desymmetrization; Epibatidine; 7-azabicyclo[2.2.1]heptane
ID Code:61007
Deposited On:13 Sep 2011 11:29
Last Modified:13 Sep 2011 11:29

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