3-Bromo-propenyl acetate in organic synthesis: an expeditious route to 3-alkyl-4-acetoxy-5-iodomethyl isoxazolidines |
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| Authors: | Marco Lombardo Gabriele Rispoli Claudio Trombini |
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| Institution: | a University of Bologna, Department of Chemistry ‘G. Ciamician’, via Selmi 2, 40126 Bologna, Italy
b University of Pune, Department of Chemistry, Garware Research Centre, Pune 411 007, India |
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| 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. |
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| Keywords: | Nitrones α-Hydroxyallylation Trimethylsilyl triflate Iodocyclization 4-Acetoxy-5-iodomethyl isoxazolidines |
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