Synthesis and stereochemistry of spiro-dihydropyran derivatives derived from bicyclo[2.2.1]heptane
Article first published online: 2 SEP 2010
Copyright © 1969 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Recueil des Travaux Chimiques des Pays-Bas
Volume 88, Issue 1, pages 62–70, 1969
How to Cite
de Boer, Th. J., van Velzen, J.C. and Kruk, C. (1969), Synthesis and stereochemistry of spiro-dihydropyran derivatives derived from bicyclo[2.2.1]heptane. Recl. Trav. Chim. Pays-Bas, 88: 62–70. doi: 10.1002/recl.19690880110
- Issue published online: 2 SEP 2010
- Article first published online: 2 SEP 2010
- Manuscript Received: 11 JUL 1968
The addition of acrolein to norcamphene leads to an exo-oxa spiro compound (Scheme 1, VIa). The corresponding endo-isomer VIb can be obtained from norbornanone X and methoxybutenyne XIII via the sequence of reactions outlined in Scheme 2. Because the steric course in some crucial steps is known, the endo structure of VIb can be established.
An alternative route leading to the exo-oxa. spiro compound IXa, starting with norbornanone is given in Scheme 3. Another route to predominantly endo-oxa compounds from norbornanone is given in Scheme 4.