Addition of indolyl and pyrrolyl grignard reagents to 1-acylpyridinium salts.
Certain indolyl and pyrrolyl Grignard reagents add to 1-acyl salts of 4-methoxy-3-(triisopropylsilyl)pyridine to give the corresponding 1-acyl-2-heteroaryl-2,3-dihydro-4-pyridones in good to high yield. When the 1-acyl group contained a chiral auxiliary, (+/-)-trans-2-(alpha-cumyl)cyclohexyloxy, addition of the indolyl Grignards resulted in a separable mixture of diastereomeric 2,3-dihydro-4-pyridones.
Kuethe
Jeffrey T
JT
Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.
Comins
Daniel L
DL
D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D007211:Indoles; D009942:Organometallic Compounds; D011726:Pyridinium Compounds; D011758:Pyrroles