The Journal of Organic Chemistry

Synthesis and synthetic utility of 1-acyl-5-(trialkylsilyl)-1, 2-dihydropyridines. A synthesis of (.+-.)-elaeokanine A

DL Comins, YC Myoung

Index: Comins, Daniel L.; Myoung, Young Chan Journal of Organic Chemistry, 1990 ,  vol. 55,  # 1  p. 292 - 298

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Citation Number: 63

Abstract

The regioselective addition of Grignard reagents to the phenoxycarbonyl salts of 3- (trialkylsilyl) pyridines was studied. Most of the 3-(trialkylsilyl) pyridine salts gave a mixture of dihydropyridines on reaction with aliphatic Grignard reagents. However, all reactions using alkyl or aryl Grignard reagents and the 1-phenoxycarbonyl salt of 3-(triisopropylsilyl) pyridine, or 4-chloro-3-(triisopropylsilyl) pyridine, gave exclusively 1, 2-dihydropyridines ...