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Please login or sign up for a free trial to access the full content. Intermolecular Triple Domino Michael/Michael/Aldol Reactions

DOI: 10.1055/sos-SD-204-00032

Mase, N.Science of Synthesis: Asymmetric Organocatalysis, (20121206.

Triple domino reactions of the three components propanal, cinnamaldehyde, and alkenes 270 proceed via an organocatalytic Michael/Michael/aldol sequence, affording the cyclohexene derivatives 271 bearing four stereogenic centers with excellent enantioselectivities in good to moderate yields.[‌282‌,‌284‌,‌285‌] These products can be used as building blocks in organic synthesis. The process consists of an enamine-based Michael reaction followed by an iminium-based Michael reaction and an enamine-based aldol condensation reaction (Scheme 61). Similar domino Michael/Michael/aldol reactions[‌184‌,‌186‌,‌286‌‌291‌] and other triple domino reactions[‌292‌] have also been reported.

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