The reaction of diethyl ethylidenemalonate (3) with 9-but-2-enyl-9-borabicyclo[3.3.1]nonane and but-2-enyltitanium reagents produces the threo-adduct (4) predominantly in a ratio of 9 : 1; similarly, the reaction of ethyle α-cyanocrotonate (5) with but-2-enyl-titanium, -zirconium, and -magnesium reagents gives the threo-adduct (6) preferentially in a ratio of 4 : 1.
Y. Yamamoto, S. Nishii and K. Maruyama, J. Chem. Soc., Chem. Commun., 1985, 386 DOI: 10.1039/C39850000386
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