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Updated: Apr 5, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Site-Selective Conjugate Addition Through Catalytic Generation of Ion-Pairing Intermediates
Daisuke Uraguchi1, Takashi Ooi2
1Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo cho, Chikusa ku, Nagoya, Aichi, 464-8602, JAPAN.
Abstract:
Site-selectivity in conjugate addition reactions is tightly associated with the principle of vinylogy. Various vinylogous nucleophiles and electrophiles have been applied to stereoselective conjugate additions directed by chiral small-molecule catalysts. This chapter focuses on the systems that control site- and stereoselectivity via chiral ion-pairing intermediates under organocatalytic conditions and describes individual vinylogous substrates in a separate section. Although site-selectivity originates largely from the intrinsic stereoelectronic nature of individual substrates, catalyst-controlled site-selectivity can be attained in certain cases.
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