… α-Addition of Alkynyl and Alkenyl Grignard Reagents to 1-Alkoxycarbonylpyridinium Salts and Its Application to Synthesis of 1-Azabicycloalkanes and (±)-Solenopsin …

R Yamaguchi, Y Nakazono, T Matsuki, E Hata…

Index: Yamaguchi, Ryohei; Nakazono, Yutaka; Matsuki, Toshitsugu; Hata, Ei-ichiro; Kawanisi, Mituyosi Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 1 p. 215 - 222

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Citation Number: 68

Abstract

Nucleophilic addition of a variety of alkynyl and alkenyl Grignard reagents to 1- methoxycarbonylpyridinium chloride takes place at the α-position in a highly regioselective manner to give 2-substituted 1-methoxycarbonyl-1, 2-dihydropyridines exclusively, while, with alkyl Grignard reagents, a lack of the regioselectivity is observed. These results may be explained by the HSAB principle. The high α-regioselectivity is preserved in the cases of 2 ...