Dhavale, Dilip D. ; Gentilucci, Luca ; Piazza, Maria Giulia ; Trombinl, Claudio (1992) Iodocyclization of homoallylic hydroxylamines derived from D-glyceraldehyde Liebigs Annalen der Chemie, 1992 (12). pp. 1289-1295. ISSN 0170-2041
Full text not available from this repository.
Official URL: http://onlinelibrary.wiley.com/doi/10.1002/jlac.19...
Related URL: http://dx.doi.org/10.1002/jlac.1992199201213
Abstract
The reaction of allylmagnesium chloride with nitrone 1 derived from D-glyceraldehyde affords two diastereoisomeric homoallylic hydroxylamines 2a and 3a which, after separation and O-silylation, are subjected to iodocyclization using N-iodosuccinimide. The stereochemical outcome of the cyclization reaction was found to be different; thus, the hydroxylamine 2b is converted into a mixture of cis- and trans-isoxazolidines 10 and 11 in which the trans product prevails, whereas 3b is stereoselectively converted into the cis product 12. The final 5-(iodomethyl)isoxazolidines 10-12 may be easily subjected to further studies; for example they undergo iodine displacement by treatment with azide, phthalimide, and acetate ions to give 13-16, formal precursors of deoxy-amino-hexitols. As an example, 1-O-acetyl-3,4-dideoxy-5,6-O-(1-methylethylidene)-4-[(phenylmethyl)amino]-D-lyxo-hexitol (17) is synthesized.
Item Type: | Article |
---|---|
Source: | Copyright of this article belongs to John Wiley & Sons, Inc. |
Keywords: | Nitrones; Iodocyclization Of Hydroxylamines; Isoxazolidines |
ID Code: | 9602 |
Deposited On: | 02 Nov 2010 11:47 |
Last Modified: | 01 Jun 2011 10:36 |
Repository Staff Only: item control page