Enantioselective copper‐catalyzed 1,4‐additions of organometallic reagents are useful components of domino reactions. Enolates resulting from such additions readily react with a range of electrophilic reagents, such as aldehydes and acetals, alkyl and allyl halides and halide surrogates, epoxides, imines, nitroalkenes, and α,β‐unsaturated carbonyl compounds. The aim of this review is to give an overview of domino transformations based on Cu‐catalyzed conjugate addition. Special emphasis is placed on the most recent work and also on that utilized in the synthesis of complex target molecules.
Cu–Taniaphos‐catalyzed enantioselective addition of Grignard reagents to cyclic enones leads to chiral magnesium enolates. These enolates add to N‐protected imines directly, or through in situ transformation to silyl enol ethers. Diastereoselectivity of the addition depends on the nitrogen protecting group of the imine. Diastereoisomers of the resulting β‐amino carbonyl compounds can be separated and are obtained in acceptable yields and in high enantiomeric purities (up to 99:1 er).
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