In the cyclisation of 4-methyldec-4-enal (2) to 3-methyl-2-pentylcyclopentanone (3), catalysed by stannic chloride, the Z-aldehyde (2-Z) forms the cis-ketone (3-c) and the E-aldehyde (2-E) the trans-ketone (3-t); this is an example of a geometrical factor of general importance.
R. C. Cookson and S. A. Smith, J. Chem. Soc., Chem. Commun., 1979, 145 DOI: 10.1039/C39790000145
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