First example of carbohydrate-based Prins cyclization: a novel class of sugar-annulated tetrahydropyrans

Yadav, J. S. ; Subba Reddy, B. V. ; Pratap Singh, Ashutosh ; Chaya, Dudhmal N. ; Chatterjee, Deepak ; Kunwar, A. C. (2010) First example of carbohydrate-based Prins cyclization: a novel class of sugar-annulated tetrahydropyrans Tetrahedron Letters, 51 (11). pp. 1475-1478. 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/j.tetlet.2010.01.028

Abstract

The secondary homoallylic alcohol derived from d-glucose undergoes smooth coupling with aldehydes in the presence of molecular iodine under mild reaction conditions to produce 7-iodofurano[3,2-b]pyrans in good yields. This method is highly stereoselective, affording cis-tetrahydropyrans exclusively.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Prins Cyclization; Molecular Iodine; Oxabicycles; 7-iodofurano[3,2-b]pyrans
ID Code:58777
Deposited On:02 Sep 2011 03:39
Last Modified:02 Sep 2011 03:39

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