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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