Lombardo, Marco ; Rispoli, Gabriele ; Licciulli, Sebastiano ; Trombini, Claudio ; Dhavale, Dilip D. (2005) 3-bromo-propenyl acetate in organic synthesis: an expeditious route to 3-alkyl-4-acetoxy-5-iodomethyl isoxazolidines Tetrahedron Letters, 46 (22). pp. 3789-3792. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.04.004
Abstract
N-Trimethylsilyloxy-N-benzyl-1-alkyl-2-acetoxy-3-buten-1-amines 13, obtained in good yields and moderate diastereoselectivities by TMSOTf promoted α-acetoxyallylation of nitrones using metallic zinc and 3-bromo-propenyl acetate 11, are exploited in a stereospecific 5-exo-trig iodocyclization reaction to afford 4,5-cis-3-alkyl-4-acetoxy-5-iodomethyl isoxazolidines 14, promising starting materials for the synthesis of pyrrolidine azasugars.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Nitrones; α-hydroxyallylation; Trimethylsilyl Triflate; Iodocyclization; 4-acetoxy-5-iodomethyl Isoxazolidines |
| ID Code: | 9741 |
| Deposited On: | 02 Nov 2010 10:44 |
| Last Modified: | 31 May 2011 11:54 |
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