Cerium chloride-promoted nucleophilic addition of grignard reagents to ketones an efficient method for the synthesis of tertiary alcohols

✍ Scribed by Tsuneo Imamoto; Nobuyuki Takiyama; Kimikazu Nakamura

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 248 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)94945-1

✦ Synopsis

In the presence of anhydrous cerium(III1 chloride, Grignard reagents react with ketones to afford addition products in high yields, even though the substrates are susceptible to abnormal reactions with Grignard reagents alone.

The reaction of Grignard reagents with carbonyl

Sympounds is well-known as one of the most versatile methods for the synthesis of alcohols. Nevertheless, the reaction is often accompanied by so-called abnormal Grignard reactions (enolization, reduction, condensation, conjugate addition etc.), and in some cases they prevail over "normal" addition to result in very poor yield of desired alcohols. Recently selective 1,2-addition of organolanthanoid complexes to d,g-enones has been reported. a1 Ref. 2c,d. b) K. Yokoo, Y. Yamanaka, T. Fukagawa, H. Taniguchi, and Y.