Intra-molecular nitrone-olefin cycloaddition of D-glucose derived allylic alcohol: synthesis of new aminocyclohexitols

Chakraborty, Chaitali ; Vyavahare, Vinod P. ; Dhavale, Dilip D. (2007) Intra-molecular nitrone-olefin cycloaddition of D-glucose derived allylic alcohol: synthesis of new aminocyclohexitols Tetrahedron, 63 (48). pp. 11984-11990. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tet.2007.09.011

Abstract

Diastereo- and regioselelective intra-molecular nitrone-olefin cycloaddition reaction of in situ generated N-benzylnitrones, obtained from D-glucose derived precursors 5a/5b furnished dihydroxy functionalized isoxazolidines. The N-O bond reductive cleavage and removal of N/O-benzyl groups led to the formation of stereochemically well defined aminocyclohexitols.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Cyclitols; Nitrones; Isoxazolidines; Carbohydrates
ID Code:9581
Deposited On:02 Nov 2010 11:51
Last Modified:31 May 2011 11:50

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