THE ADDITION OF METALLO-ENOLATES TO CHIRAL 1-ACYLPYRIDINIUM SALTS - AN ASYMMETRIC-SYNTHESIS OF (-)-SEDAMINE

被引：54

作者：

COMINS, DL

HONG, H

机构：

[1] Department of Chemistry, North Carolina State University, Raleigh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 19期

关键词：

D O I：

10.1021/jo00071a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetically useful 2-(2-oxoalkyl)-2,3-dihydro-4-pyridones are prepared in high diastereomeric excess by addition of ketone metallo enolates to chiral 1-acyl-4-methoxypyridinium salts.

引用

页码：5035 / 5036

页数：2

共 28 条

[1] REGIOSELECTIVE SYNTHESIS OF 4-ALKYLPYRIDINES VIA 1,4-DIHYDROPYRIDINE DERIVATIVES FROM PYRIDINE
AKIBA, K
ISEKI, Y
WADA, M
[J]. TETRAHEDRON LETTERS, 1982, 23 (04) : 429 - 432
[2] AN EFFICIENT ASYMMETRIC-SYNTHESIS OF 1-ACYL-2-ALKYL-1,2-DIHYDROPYRIDINES
COMINS, DL
HONG, H
SALVADOR, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) : 7197 - 7199
[3] CHIRAL DIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC-SYNTHESIS OF (+)-ELAEOKANINE-A AND (+)-ELAEOKANINE-C
COMINS, DL
HONG, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) : 6672 - 6673
[4] 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
GOEHRING, RR
JOSEPH, SP
OCONNOR, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) : 2574 - 2576
[5] REGIOSELECTIVE ADDITION OF TITANIUM ENOLATES TO 1-ACYLPYRIDINIUM SALTS - A CONVENIENT SYNTHESIS OF 4-(2-OXOALKYL)PYRIDINES
COMINS, DL
BROWN, JD
[J]. TETRAHEDRON LETTERS, 1984, 25 (31) : 3297 - 3300
[6] PREPARATION OF 1-(TERT-BUTOXYCARBONYL)-2,6-DIALKYL-2,3-DIHYDRO-4-PYRIDONES - A STEREOCONTROLLED SYNTHESIS OF (+/-)-MYRTINE
COMINS, DL
LAMUNYON, DH
[J]. TETRAHEDRON LETTERS, 1989, 30 (38) : 5053 - 5056
[7] N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - SYNTHESIS OF (+/-)-SEPTICINE AND (+/-)-TYLOPHORINE
COMINS, DL
MORGAN, LA
[J]. TETRAHEDRON LETTERS, 1991, 32 (42) : 5919 - 5922
[8] PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES
COMINS, DL
DEHGHANI, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (42) : 6299 - 6302
[9] ENANTIOPURE 2,3-DIHYDRO-4-PYRIDONES AS SYNTHETIC INTERMEDIATES - ASYMMETRIC SYNTHESES OF THE QUINOLIZIDINE ALKALOIDS (+)-MYRTINE, (-)-LASUBINE-I, AND (+)-SUBCOSINE-I
COMINS, DL
LAMUNYON, DH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) : 5807 - 5809
[10] AN EFFICIENT PREPARATION OF (+)-TRANS-2-(ALPHA-CUMYL)CYCLOHEXANOL ((+)-TCC) - A PRACTICAL ALTERNATIVE TO (+)-8-PHENYLMENTHOL
COMINS, DL
SALVADOR, JM
[J]. TETRAHEDRON LETTERS, 1993, 34 (05) : 801 - 804

← 1 2 3 →