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Synthesis of chiral 1,4-dihydropyridines by diastereoface-selective asymmetric addition to nicotinic amides

✍ Scribed by Shinji Yamada; Mayumi Ichikawa

Book ID: 104261466
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 227 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00683-8

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✦ Synopsis

Diastereoface-selective asymmetric addition of organometallic reagents to pyridinium salts of 1 and 2 was performed to give chiral 1,4-dihydropyridines in good regio-and stereoselectivities. The absolute configuration of the newly-produced chiral center was determined by X-ray analysis after derivation to menthyloxycarbamate 10. Neighboring group participation of the thiocarbonyl group to the pyridinium nucleus was predicted by PM3 calculations of the intermediary pyridinium salts, which may play an important role in the generation of stereoselectivity.

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