Site-Selective Conjugate Addition Through Catalytic Generation of Ion-Pairing Intermediates.
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.
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo cho, Chikusa ku, Nagoya, Aichi, 464-8602, JAPAN.
Daisuke
D
Uraguchi
Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, and CREST, Japan Science and Technology Agency (JST), Furo cho, Chikusa ku, Nagoya, Aichi, 464-8602, JAPAN. tooi@apchem.nagoya-u.ac.jp.
Takashi
T
Ooi
Asymmetric catalysis; Ion-pairing; Organocatalysis; Vinylogy