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THE CONVERSION OF AN AZIRIDINE TO A BETA-LACTAM
被引:57
作者
:
CHAMCHAANG, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
CHAMCHAANG, W
[
1
]
PINHAS, AR
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
PINHAS, AR
[
1
]
机构
:
[1]
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
1990年
/ 55卷
/ 09期
关键词
:
D O I
:
10.1021/jo00296a070
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
A one-pot, inert atmosphere conversion of an aziridine to a β-lactam using nickel tetracarbonyl as the carbonyl source is described. In this reaction it is the less substituted carbon-nitrogen bond which is carbonylated. The proposed mechanism for this reaction requires that a nickel acylate complex attack an alkyl iodide with inversion of configuration. Iron carbonyl complexes are unsuccessful in this carbonylation process. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码:2943 / 2950
页数:8
相关论文
共 25 条
[1]
STRUCTURE OF CEPHALOSPORIN C
ABRAHAM, EP
论文数:
0
引用数:
0
h-index:
0
ABRAHAM, EP
NEWTON, GGF
论文数:
0
引用数:
0
h-index:
0
NEWTON, GGF
[J].
BIOCHEMICAL JOURNAL,
1961,
79
(02)
: 377
-
&
[2]
REGIOSPECIFIC METAL-CATALYZED RING EXPANSION OF AZIRIDINES TO BETA-LACTAMS
ALPER, H
论文数:
0
引用数:
0
h-index:
0
机构:
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
ALPER, H
URSO, F
论文数:
0
引用数:
0
h-index:
0
机构:
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
URSO, F
SMITH, DJH
论文数:
0
引用数:
0
h-index:
0
机构:
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
SMITH, DJH
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1983,
105
(22)
: 6737
-
6738
[3]
REGIOSPECIFIC SYNTHESIS OF ALPHA-METHYLENE-BETA-LACTAMS BY A HOMOGENEOUS PALLADIUM CATALYZED RING EXPANSION-CARBONYLATION REACTION
ALPER, H
论文数:
0
引用数:
0
h-index:
0
ALPER, H
HAMEL, N
论文数:
0
引用数:
0
h-index:
0
HAMEL, N
[J].
TETRAHEDRON LETTERS,
1987,
28
(28)
: 3237
-
3240
[4]
Baldwin J., 1983, TETRAHEDRON, V39, P2445
[5]
NATURALLY-OCCURRING BETA-LACTAMASE INHIBITORS WITH ANTIBACTERIAL ACTIVITY
BROWN, AG
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BROWN, AG
BUTTERWORTH, D
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BUTTERWORTH, D
COLE, M
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
COLE, M
HANSCOMB, G
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
HANSCOMB, G
HOOD, JD
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
HOOD, JD
READING, C
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
READING, C
[J].
JOURNAL OF ANTIBIOTICS,
1976,
29
(06)
: 668
-
669
[6]
ENANTIOSPECIFIC AND STEREOSPECIFIC RHODIUM(I)-CATALYZED CARBONYLATION AND RING EXPANSION OF AZIRIDINES - ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND THE KINETIC RESOLUTION OF AZIRIDINES
CALET, S
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
CALET, S
URSO, F
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
URSO, F
ALPER, H
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
ALPER, H
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(03)
: 931
-
934
[7]
A ONE-POT CONVERSION OF AN AZIRIDINE TO A BETA-LACTAM USING NICKEL TETRACARBONYL
CHAMCHAANG, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
CHAMCHAANG, W
PINHAS, AR
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
PINHAS, AR
[J].
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1988,
(11)
: 710
-
711
[8]
BASE-CATALYZED CARBOXYLATION OF ORGANIC HALIDES NICKEL CARBONYL IN PROTIC MEDIA
COREY, EJ
论文数:
0
引用数:
0
h-index:
0
COREY, EJ
HEGEDUS, LS
论文数:
0
引用数:
0
h-index:
0
HEGEDUS, LS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1969,
91
(05)
: 1233
-
&
[9]
A FACILE SYNTHESIS OF METHANESULFONATE ESTERS
CROSSLAN.RK
论文数:
0
引用数:
0
h-index:
0
CROSSLAN.RK
SERVIS, KL
论文数:
0
引用数:
0
h-index:
0
SERVIS, KL
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1970,
35
(09)
: 3195
-
&
[10]
DEYRUP JA, 1983, HETEROCYCLIC COMPO 1, V42
←
1
2
3
→
共 25 条
[1]
STRUCTURE OF CEPHALOSPORIN C
ABRAHAM, EP
论文数:
0
引用数:
0
h-index:
0
ABRAHAM, EP
NEWTON, GGF
论文数:
0
引用数:
0
h-index:
0
NEWTON, GGF
[J].
BIOCHEMICAL JOURNAL,
1961,
79
(02)
: 377
-
&
[2]
REGIOSPECIFIC METAL-CATALYZED RING EXPANSION OF AZIRIDINES TO BETA-LACTAMS
ALPER, H
论文数:
0
引用数:
0
h-index:
0
机构:
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
ALPER, H
URSO, F
论文数:
0
引用数:
0
h-index:
0
机构:
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
URSO, F
SMITH, DJH
论文数:
0
引用数:
0
h-index:
0
机构:
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
BP RES CTR,SUNBURY THAMES TW16 7LN,MIDDX,ENGLAND
SMITH, DJH
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1983,
105
(22)
: 6737
-
6738
[3]
REGIOSPECIFIC SYNTHESIS OF ALPHA-METHYLENE-BETA-LACTAMS BY A HOMOGENEOUS PALLADIUM CATALYZED RING EXPANSION-CARBONYLATION REACTION
ALPER, H
论文数:
0
引用数:
0
h-index:
0
ALPER, H
HAMEL, N
论文数:
0
引用数:
0
h-index:
0
HAMEL, N
[J].
TETRAHEDRON LETTERS,
1987,
28
(28)
: 3237
-
3240
[4]
Baldwin J., 1983, TETRAHEDRON, V39, P2445
[5]
NATURALLY-OCCURRING BETA-LACTAMASE INHIBITORS WITH ANTIBACTERIAL ACTIVITY
BROWN, AG
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BROWN, AG
BUTTERWORTH, D
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BUTTERWORTH, D
COLE, M
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
COLE, M
HANSCOMB, G
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
HANSCOMB, G
HOOD, JD
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
HOOD, JD
READING, C
论文数:
0
引用数:
0
h-index:
0
机构:
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
BEECHAM PHARM RES DIV,BETCHWORTH,SURREY,ENGLAND
READING, C
[J].
JOURNAL OF ANTIBIOTICS,
1976,
29
(06)
: 668
-
669
[6]
ENANTIOSPECIFIC AND STEREOSPECIFIC RHODIUM(I)-CATALYZED CARBONYLATION AND RING EXPANSION OF AZIRIDINES - ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS AND THE KINETIC RESOLUTION OF AZIRIDINES
CALET, S
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
CALET, S
URSO, F
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
URSO, F
ALPER, H
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 9B4,ONTARIO,CANADA
ALPER, H
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1989,
111
(03)
: 931
-
934
[7]
A ONE-POT CONVERSION OF AN AZIRIDINE TO A BETA-LACTAM USING NICKEL TETRACARBONYL
CHAMCHAANG, W
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
CHAMCHAANG, W
PINHAS, AR
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
UNIV CINCINNATI,DEPT CHEM,CINCINNATI,OH 45221
PINHAS, AR
[J].
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS,
1988,
(11)
: 710
-
711
[8]
BASE-CATALYZED CARBOXYLATION OF ORGANIC HALIDES NICKEL CARBONYL IN PROTIC MEDIA
COREY, EJ
论文数:
0
引用数:
0
h-index:
0
COREY, EJ
HEGEDUS, LS
论文数:
0
引用数:
0
h-index:
0
HEGEDUS, LS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1969,
91
(05)
: 1233
-
&
[9]
A FACILE SYNTHESIS OF METHANESULFONATE ESTERS
CROSSLAN.RK
论文数:
0
引用数:
0
h-index:
0
CROSSLAN.RK
SERVIS, KL
论文数:
0
引用数:
0
h-index:
0
SERVIS, KL
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1970,
35
(09)
: 3195
-
&
[10]
DEYRUP JA, 1983, HETEROCYCLIC COMPO 1, V42
←
1
2
3
→