将吲哚基和吡咯基格氏试剂添加到1-酰基吡啶鎓盐中。

Addition of indolyl and pyrrolyl grignard reagents to 1-acylpyridinium salts.

作者信息

Kuethe Jeffrey T, Comins Daniel L

机构信息

Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, USA.

出版信息

J Org Chem. 2004 Apr 16;69(8):2863-6. doi: 10.1021/jo049943v.

DOI:10.1021/jo049943v

PMID:15074941

Abstract

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.

摘要

某些吲哚基和吡咯基格氏试剂与4-甲氧基-3-(三异丙基甲硅烷基)吡啶的1-酰基盐反应，能以良好至高收率得到相应的1-酰基-2-杂芳基-2,3-二氢-4-吡啶酮。当1-酰基含有手性助剂(+/-)-反式-2-(α-异丙基苯基)环己氧基时，吲哚基格氏试剂的加入会产生非对映异构的2,3-二氢-4-吡啶酮的可分离混合物。