Regioselective and diastereoselective phosphine-catalysed [3+2] cycloadditions to 5-methylenehydantoins: reversal of regioselectivity using chiral N-2-butynoyl-(4S)-benzyloxazolidinone

doi:10.1016/S0040-4039(02)01245-5

Tetrahedron Letters

Volume 43, Issue 34, 19 August 2002, Pages 5953-5956

https://doi.org/10.1016/S0040-4039(02)01245-5 Get rights and content

Abstract

The phosphine-catalysed [3+2] cycloaddition of 5-methylenehydantoins 1 with the ylides 2a and 2b gives spirocyclic products with reverse regioselectivities; the latter ylide gives optically active products.

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Acknowledgments

We thank the University of Wollongong for a Ph.D. scholarship to T.Q.P.

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Citation Excerpt :
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Regioselective and diastereoselective phosphine-catalysed [3+2] cycloadditions to 5-methylenehydantoins: reversal of regioselectivity using chiral N-2-butynoyl-(4S)-benzyloxazolidinone

Abstract

Section snippets

Acknowledgments

Tetrahedron Lett.

Pest. Biochem. Physiol.

Tetrahedron

Org. Lett.

J. Org. Chem.

Chem. Commun.

Chem. Commun.

Chem. Commun.