Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes

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doi:10.1071/CH07282

Synthesis of 5-Aryloxazolidines via 1,3-Dipolar Cycloaddition Reaction of a Non-Stabilized Azomethine Ylide with Aromatic Aldehydes

John H. Ryan ^A ^C, Nadia Spiccia ^A, Leon S.-M. Wong ^A, Andrew B. Holmes ^B

^A CSIRO Molecular and Health Technologies, Bag 10, Clayton South VIC 3169, Australia.
^B School of Chemistry, Bio21 Institute, University of Melbourne, 30 Flemington Road, Parkville VIC 3010, Australia.
^C Corresponding author. Email: jack.ryan@csiro.au





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Australian Journal of Chemistry 60(12) 898–904 http://dx.doi.org/10.1071/CH07282
Submitted: 7 August 2007 Accepted: 21 September 2007 Published online: 4 December 2007

Abstract

The 1,3-dipolar cycloaddition reaction of a non-stabilized azomethine ylide 4a, formed in situ from N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine 5 and a catalytic amount of trifluoroacetic acid, with aromatic aldehydes 3 gives rise to N-benzyl-5-aryloxazolidines 1. Under these conditions, 4-hydroxybenzaldehyde 3p undergoes two-fold addition of azomethine ylide 4a to afford bis adduct 11.