Novel Use of N-Carboalkoxy α,β-Unsaturated Iminium Ions as Dienophiles in Diels-Alder Reactions

Patrick D. O’Connor; Karsten Körber; Margaret A. Brimble

doi:10.1055/s-2008-1072658

LETTER

Novel Use of N-Carboalkoxy α,β-Unsaturated Iminium Ions as Dienophiles in Diels-Alder Reactions

Patrick D. O’Connor, Karsten Körber, Margaret A. Brimble*
Department of Chemistry, The University of Auckland, 23 Symonds Street, Auckland 1142, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Abstract

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Abstract

Tricyclic spiro-N,O-acetals have been assembled in a single step by cycloaddition of hydroxymethyl-substituted dienes to iminium ion activated dienophiles that were generated by acidolysis of α,β-unsaturated-N-carboalkoxy-N,O-acetals or β-methoxymethyl-N-carboalkoxy-enamines. The cycloaddition was conducted using Sc(OTf)₃ as a mild Lewis acid affording the endo adducts in moderate yields.

Key words

iminium ion - Diels-Alder - cycloaddition

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References and Notes

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