This paper reports the utility of simple metal alkoxides for the catalytic, stereoselective hetero-aldol−Tishchenko reaction (eq 1). Choice of metal alkoxide is crucial to achieving high efficiency and stereoselectivity. Whereas NaO- t -Bu is an effective catalyst, delivering one product in 68% yield and 99:1 stereoselection, Sm(O- i -Pr) 3 is less effective and delivers the same product in 42% yield with 4:1 stereoselection.
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Mascarenhas et al. (1999) studied this question.
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