Inter- and intramolecular Horner-Wadsworth-Emmons reactions of 5-(diethoxyphosphoryl)-1-acyl-2-alkyl(aryl)-2,3-dihydro-4-pyridones

被引:24
作者
Comins, DL [1 ]
Ollinger, CG [1 ]
机构
[1] N Carolina State Univ, Dept Chem, Raleigh, NC 27695 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(01)00690-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dihydropyridones of the type I were converted to their C-5 alkylidene derivatives 2 by a reaction sequence involving phosphorylation, conjugate reduction or addition to provide piperidones 4, and then olefination via a Horner-Wadsworth-Emmons reaction. An intramolecular version of this method was used to prepare trans-bicyclic enone 13. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4115 / 4118
页数:4
相关论文
共 18 条
[1]   OLEFIN SYNTHESIS WITH ORGANIC PHOSPHONATE CARBANIONS [J].
BOUTAGY, J ;
THOMAS, R .
CHEMICAL REVIEWS, 1974, 74 (01) :87-99
[2]   Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones [J].
Comins, DL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) :1491-1500
[3]   Synthesis and reactivity of N-acyl-5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones [J].
Comins, DL ;
Hiebel, AC ;
Huang, SL .
ORGANIC LETTERS, 2001, 3 (05) :769-771
[4]   IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids:: Asymmetric synthesis of (+)-luciduline [J].
Comins, DL ;
Brooks, CA ;
Al-awar, RS ;
Goehring, RR .
ORGANIC LETTERS, 1999, 1 (02) :229-231
[5]   Asymmetric synthesis of the Lycopodium alkaloid, Na-acetyl-Nb-methylphlegmarine [J].
Comins, DL ;
Libby, AH ;
Al-awar, RS ;
Foti, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2184-2185
[6]   Asymmetric addition of Grignard reagents to chiral 1-acylpyridinium salts: A chiral auxiliary study [J].
Comins, DL ;
GuerraWeltzien, L .
TETRAHEDRON LETTERS, 1996, 37 (22) :3807-3810
[7]   GRIGNARD ADDITION TO 1-ACYL SALTS OF CHIRAL 4-ALKOXYPYRIDINES - A NEW ENANTIOSELECTIVE PREPARATION OF 2-ALKYL-2,3-DIHYDRO-4-PYRIDONES [J].
COMINS, DL ;
LAMUNYON, DH .
TETRAHEDRON LETTERS, 1994, 35 (40) :7343-7346
[8]  
COMINS DL, 1986, TETRAHEDRON LETT, V27, P4549
[9]   ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].
COMINS, DL ;
JOSEPH, SP ;
GOEHRING, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (11) :4719-4728
[10]   REGIOSPECIFIC SUBSTITUTION OF N-ACYL-2,3-DIHYDRO-4-PYRIDONES AT C-5 VIA HALOGENATION AND CROSS-COUPLING [J].
COMINS, DL ;
JOSEPH, SP ;
CHEN, XH .
TETRAHEDRON LETTERS, 1995, 36 (50) :9141-9144