Science of Synthesis

Liu, L.; Wang, D.; Li, C. -J., Science of Synthesis: Stereoselective Synthesis, (2011) 2, 611.

Under catalysis by a disulfonimide (e.g., ‌38‌), 2-methylpropanoate- and acetate-derived ketene acetals (e.g., ‌91‌) react with aldehydes to provide the corresponding aldol products (e.g., ‌92‌) in excellent yields and high enantioselectivities (‌Scheme 39‌).[‌43‌] Turnover numbers of up to 8800 can be achieved. Such numbers are rare in organocatalysis and unprecedented in the enantioselective Mukaiyama aldol reaction. This kind of catalyst is a powerful practical tool for activation of unactivated substrates such as simple aldehydes.

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References