Stepwise Palladium-Catalyzed 1, 4-Addition of Arylboronic Acids to Enones and Regioselective Baeyer-Villiger Oxidation for Enantioselective Synthesis of. BETA.- …

K Kobayashi, T Nishikata, Y Yamamoto…

Index: Kobayashi, Kenya; Nishikata, Takashi; Yamamoto, Yasunori; Miyaura, Norio Bulletin of the Chemical Society of Japan, 2008 , vol. 81, # 8 p. 1019 - 1025

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Citation Number: 14

Abstract

Baeyer–Villiger oxidation of chiral β-diaryl ketones synthesized by 1, 4-addition of arylboronic acids to β-aryl-α, β-unsaturated ketones catalyzed by a palladium (2+)– chiraphos complex provided optically active β-diaryl esters up to 98% ee. The protocol was applied to the synthesis of a potent competitive muscarinic receptor antagonist,(R)- tolterodine (21), which has a chiral center consisting of two aryl rings.