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

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 25期

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

页码：4115 / 4118

页数：4

共 18 条

[1] OLEFIN SYNTHESIS WITH ORGANIC PHOSPHONATE CARBANIONS
BOUTAGY, J
THOMAS, R
[J]. CHEMICAL REVIEWS, 1974, 74 (01) : 87 - 99
[2] Asymmetric synthesis and synthetic utility of 2,3-dihydro-4-pyridones
Comins, DL
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (06) : 1491 - 1500
[3] Synthesis and reactivity of N-acyl-5-(1-hydroxyalkyl)-2,3-dihydro-4-pyridones
Comins, DL
Hiebel, AC
Huang, SL
[J]. ORGANIC LETTERS, 2001, 3 (05) : 769 - 771
[4] IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids:: Asymmetric synthesis of (+)-luciduline
Comins, DL
Brooks, CA
Al-awar, RS
Goehring, RR
[J]. ORGANIC LETTERS, 1999, 1 (02) : 229 - 231
[5] Asymmetric synthesis of the Lycopodium alkaloid, Na-acetyl-Nb-methylphlegmarine
Comins, DL
Libby, AH
Al-awar, RS
Foti, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) : 2184 - 2185
[6] Asymmetric addition of Grignard reagents to chiral 1-acylpyridinium salts: A chiral auxiliary study
Comins, DL
GuerraWeltzien, L
[J]. 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
COMINS, DL
LAMUNYON, DH
[J]. 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
COMINS, DL
JOSEPH, SP
GOEHRING, RR
[J]. 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
COMINS, DL
JOSEPH, SP
CHEN, XH
[J]. TETRAHEDRON LETTERS, 1995, 36 (50) : 9141 - 9144

← 1 2 →