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On the stereodivergent behavior observed in the staudinger reaction between methoxyketene and (E)-N-benzylidenearyl amines
被引:48
作者
:
Banik, Bimal K.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem, Edinburg, TX 78541 USA
Banik, Bimal K.
Lecea, Begona
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem, Edinburg, TX 78541 USA
Lecea, Begona
Arrieta, Ana
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem, Edinburg, TX 78541 USA
Arrieta, Ana
de Cozar, Abel
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem, Edinburg, TX 78541 USA
de Cozar, Abel
论文数:
引用数:
h-index:
机构:
Cossio, Fernando P.
机构
:
[1]
Univ Texas, Dept Chem, Edinburg, TX 78541 USA
[2]
Univ Basque Country, Dept Organ Chem 1, UPV, EHU, Donostia San Sebastian 20018, Spain
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2007年
/ 46卷
/ 17期
关键词
:
cycloaddition;
imines;
ketenes;
lactams;
transition states;
D O I
:
10.1002/anie.200605231
中图分类号
:
O6 [化学];
学科分类号
:
0703
[化学]
;
摘要
:
The answer is out there: Detailed calculations on the Staudinger reaction between methoxyketene and imines derived from aromatic amines show that the stereochemistry of the reaction is determined by an isomerization barrier that does not belong to the cycloaddition stages (see picture). (Chemical Equation Presented). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3028 / 3032
页数:5
相关论文
共 21 条
[1]
Origins of the stereodivergent outcome in the Staudinger reaction between acyl chlorides and imines
[J].
Arrieta, A
论文数:
0
引用数:
0
h-index:
0
机构:
Euskal Herriko Unibertsitatea, Kimika Fak, San Sebastian 20080, Spain
Arrieta, A
;
Lecea, B
论文数:
0
引用数:
0
h-index:
0
机构:
Euskal Herriko Unibertsitatea, Kimika Fak, San Sebastian 20080, Spain
Lecea, B
;
Cossío, FP
论文数:
0
引用数:
0
h-index:
0
机构:
Euskal Herriko Unibertsitatea, Kimika Fak, San Sebastian 20080, Spain
Cossío, FP
.
JOURNAL OF ORGANIC CHEMISTRY,
1998,
63
(17)
:5869
-5876
[2]
Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
[J].
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA
Banik, BK
;
Banik, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA
Banik, I
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA
Becker, FF
.
BIOORGANIC & MEDICINAL CHEMISTRY,
2005,
13
(11)
:3611
-3622
[3]
Synthesis of anticancer β-lactams:: mechanism of action
[J].
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Banik, BK
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Becker, FF
;
Banik, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Banik, I
.
BIOORGANIC & MEDICINAL CHEMISTRY,
2004,
12
(10)
:2523
-2528
[4]
Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines
[J].
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Banik, BK
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Becker, FF
.
TETRAHEDRON LETTERS,
2000,
41
(34)
:6551
-6554
[5]
Stereoselective synthesis of β-lactams with polyaromatic imines:: Entry to new and novel anticancer agents
[J].
Banik, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Banik, I
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Becker, FF
;
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Banik, BK
.
JOURNAL OF MEDICINAL CHEMISTRY,
2003,
46
(01)
:12
-15
[6]
DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
[J].
BECKE, AD
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Queen's University, Kingston
BECKE, AD
.
JOURNAL OF CHEMICAL PHYSICS,
1993,
98
(07)
:5648
-5652
[7]
Fast evaluation of geometries and properties of excited molecules in solution: A Tamm-Dancoff model with application to 4-dimethylaminobenzonitrile
[J].
Cammi, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
Cammi, R
;
论文数:
引用数:
h-index:
机构:
Mennucci, B
;
Tomasi, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
Tomasi, J
.
JOURNAL OF PHYSICAL CHEMISTRY A,
2000,
104
(23)
:5631
-5637
[8]
DOULBIER WR, 1996, ACCOUNTS CHEM RES, V29, P471
[9]
GEOG GI, 1993, ORGANIC CHEM LACTAMS, P295
[10]
Origin of the relative stereoselectivity of the β-lactam formation in the Staudinger reaction
[J].
Jiao, Lei
论文数:
0
引用数:
0
h-index:
0
机构:
Peking Univ, Coll Chem & Mol Engn, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
Peking Univ, Coll Chem & Mol Engn, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
Jiao, Lei
;
论文数:
引用数:
h-index:
机构:
Liang, Yong
;
论文数:
引用数:
h-index:
机构:
Xu, Jiaxi
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(18)
:6060
-6069
←
1
2
3
→
共 21 条
[1]
Origins of the stereodivergent outcome in the Staudinger reaction between acyl chlorides and imines
[J].
Arrieta, A
论文数:
0
引用数:
0
h-index:
0
机构:
Euskal Herriko Unibertsitatea, Kimika Fak, San Sebastian 20080, Spain
Arrieta, A
;
Lecea, B
论文数:
0
引用数:
0
h-index:
0
机构:
Euskal Herriko Unibertsitatea, Kimika Fak, San Sebastian 20080, Spain
Lecea, B
;
Cossío, FP
论文数:
0
引用数:
0
h-index:
0
机构:
Euskal Herriko Unibertsitatea, Kimika Fak, San Sebastian 20080, Spain
Cossío, FP
.
JOURNAL OF ORGANIC CHEMISTRY,
1998,
63
(17)
:5869
-5876
[2]
Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
[J].
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA
Banik, BK
;
Banik, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA
Banik, I
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas Pan Amer, Dept Chem, Edinburg, TX 78541 USA
Becker, FF
.
BIOORGANIC & MEDICINAL CHEMISTRY,
2005,
13
(11)
:3611
-3622
[3]
Synthesis of anticancer β-lactams:: mechanism of action
[J].
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Banik, BK
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Becker, FF
;
Banik, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Unit 89, Houston, TX 77030 USA
Banik, I
.
BIOORGANIC & MEDICINAL CHEMISTRY,
2004,
12
(10)
:2523
-2528
[4]
Unprecedented stereoselectivity in the Staudinger reaction with polycyclic aromatic imines
[J].
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Banik, BK
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Becker, FF
.
TETRAHEDRON LETTERS,
2000,
41
(34)
:6551
-6554
[5]
Stereoselective synthesis of β-lactams with polyaromatic imines:: Entry to new and novel anticancer agents
[J].
Banik, I
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Banik, I
;
Becker, FF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Becker, FF
;
Banik, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Univ Texas, MD Anderson Canc Ctr, Dept Mol Pathol, Houston, TX 77030 USA
Banik, BK
.
JOURNAL OF MEDICINAL CHEMISTRY,
2003,
46
(01)
:12
-15
[6]
DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
[J].
BECKE, AD
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Queen's University, Kingston
BECKE, AD
.
JOURNAL OF CHEMICAL PHYSICS,
1993,
98
(07)
:5648
-5652
[7]
Fast evaluation of geometries and properties of excited molecules in solution: A Tamm-Dancoff model with application to 4-dimethylaminobenzonitrile
[J].
Cammi, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
Cammi, R
;
论文数:
引用数:
h-index:
机构:
Mennucci, B
;
Tomasi, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pisa, Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
Tomasi, J
.
JOURNAL OF PHYSICAL CHEMISTRY A,
2000,
104
(23)
:5631
-5637
[8]
DOULBIER WR, 1996, ACCOUNTS CHEM RES, V29, P471
[9]
GEOG GI, 1993, ORGANIC CHEM LACTAMS, P295
[10]
Origin of the relative stereoselectivity of the β-lactam formation in the Staudinger reaction
[J].
Jiao, Lei
论文数:
0
引用数:
0
h-index:
0
机构:
Peking Univ, Coll Chem & Mol Engn, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
Peking Univ, Coll Chem & Mol Engn, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
Jiao, Lei
;
论文数:
引用数:
h-index:
机构:
Liang, Yong
;
论文数:
引用数:
h-index:
机构:
Xu, Jiaxi
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(18)
:6060
-6069
←
1
2
3
→