The Lewis acid mediated reaction of the meso-dimethylglutaric hemialdehyde (2) with pent-3-en–2-yltributyltin (1) gave the anti-Cram erythro isomer (4) predominantly, while the reaction of the (±)-isomer (3) produced the Cram erythro derivative (5) preferentially.
Y. Yamamoto, K. Taniguchi and K. Maruyama, J. Chem. Soc., Chem. Commun., 1985, 1429 DOI: 10.1039/C39850001429
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