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

John H. Ryan; Nadia Spiccia; Leon S.-M. Wong; Andrew B. Holmes

doi:10.1071/CH07282

RESEARCH ARTICLE

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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 and Andrew B. Holmes ^B

+ Author Affiliations

- Author Affiliations

^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

Australian Journal of Chemistry 60(12) 898-904 https://doi.org/10.1071/CH07282
Submitted: 7 August 2007 Accepted: 21 September 2007 Published: 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.

Acknowledgements

We thank the CSIRO (Australia), the Australian Research Council, and the Victorian Endowment for Science, Knowledge and Innovation (VESKI) for financial support. Nadia Spiccia was the recipient of a CSIRO Summer Vacation Scholarship. We also thank Dr Roger Mulder and Dr Jo Cosgriff for assistance with collection of NMR data, and Dr Carl Braybrook for interpretation of MS data.

References

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

Abstract

Acknowledgements

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