共 102 条
Lewis Acid Catalyzed SN2-Type Ring Opening of N-Activated Aziridines with Electron-Rich Arenes/Heteroarenes
被引:54
作者:

Ghorai, Manas K.
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Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

Tiwari, Deo Prakash
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Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

Jain, Nikita
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Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
机构:
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词:
ENANTIOSELECTIVE SYNTHESIS;
MESO-AZIRIDINES;
C-ARYLATION;
STEREOCONTROLLED SYNTHESIS;
CYCLIZATION REACTIONS;
EFFICIENT CATALYST;
TOSYL AZIRIDINES;
SYNTHETIC ROUTE;
DERIVATIVES;
TRANSFORMATION;
D O I:
10.1021/jo401028j
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
An efficient Lewis acid catalyzed S(N)2-type ring opening of substituted aziridines with electron-rich arenes/heteroarenes to provide substituted 2,2-diaryl/heteroarylethylamines in excellent yields and stereoselectivity (er, dr >99:1) is described.
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页码:7121 / 7130
页数:10
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共 102 条
[11]
Construction of three contiguous tertiary stereocenters from Aziridines in one step
[J].
Blyumin, Evgeniy V.
;
Gallon, Helen J.
;
Yudin, Andrei K.
.
ORGANIC LETTERS,
2007, 9 (23)
:4677-4680

Blyumin, Evgeniy V.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

Gallon, Helen J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

Yudin, Andrei K.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
[12]
Intramolecular π-π Stacking Interactions in 2-Substituted N,N-Dibenzylaziridinium Ions and Their Regioselectivity in Nucleophilic Ring-Opening Reactions
[J].
Catak, Saron
;
D'hooghe, Matthias
;
De Kimpe, Norbert
;
Waroquier, Michel
;
Van Speybroeck, Veronique
.
JOURNAL OF ORGANIC CHEMISTRY,
2010, 75 (03)
:885-896

论文数: 引用数:
h-index:
机构:

D'hooghe, Matthias
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium Univ Ghent, Ctr Mol Modeling, B-9052 Ghent, Belgium

De Kimpe, Norbert
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium Univ Ghent, Ctr Mol Modeling, B-9052 Ghent, Belgium

Waroquier, Michel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Ctr Mol Modeling, B-9052 Ghent, Belgium
QCMM Alliance, Ghent, Belgium Univ Ghent, Ctr Mol Modeling, B-9052 Ghent, Belgium

论文数: 引用数:
h-index:
机构:
[13]
C-3-symmetric tripodal tetra-amines - preparation from chiral amino alcohols via aziridines
[J].
Cernerud, M
;
Adolfsson, H
;
Moberg, C
.
TETRAHEDRON-ASYMMETRY,
1997, 8 (15)
:2655-2662

Cernerud, M
论文数: 0 引用数: 0
h-index: 0
机构:
ROYAL INST TECHNOL,DEPT CHEM,S-10044 STOCKHOLM,SWEDEN ROYAL INST TECHNOL,DEPT CHEM,S-10044 STOCKHOLM,SWEDEN

论文数: 引用数:
h-index:
机构:

Moberg, C
论文数: 0 引用数: 0
h-index: 0
机构:
ROYAL INST TECHNOL,DEPT CHEM,S-10044 STOCKHOLM,SWEDEN ROYAL INST TECHNOL,DEPT CHEM,S-10044 STOCKHOLM,SWEDEN
[14]
Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines
[J].
Cockrell, Jennifer
;
Wilhelmsen, Christopher
;
Rubin, Heather
;
Martin, Allen
;
Morgan, Jeremy B.
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2012, 51 (39)
:9842-9845

Cockrell, Jennifer
论文数: 0 引用数: 0
h-index: 0
机构:
Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA

Wilhelmsen, Christopher
论文数: 0 引用数: 0
h-index: 0
机构:
Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA

Rubin, Heather
论文数: 0 引用数: 0
h-index: 0
机构:
Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA

Martin, Allen
论文数: 0 引用数: 0
h-index: 0
机构:
Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA

Morgan, Jeremy B.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA Univ N Carolina, Dept Chem & Biochem, Wilmington, NC 28403 USA
[15]
Selective ring-opening of nonactivated amino aziridines by thiols and unusual nucleophilic substitution of a dibenzylamino group
[J].
Concellón, JM
;
Bernad, PL
;
Suárez, JR
.
JOURNAL OF ORGANIC CHEMISTRY,
2005, 70 (23)
:9411-9416

Concellón, JM
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

Bernad, PL
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

Suárez, JR
论文数: 0 引用数: 0
h-index: 0
机构: Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
[16]
Total Regioselective Transformation of Aromatic Aziridine 2-Carboxamides into 2-Aminoamides Promoted by Active Manganese
[J].
Concellon, Jose M.
;
Rodriguez-Solla, Humberto
;
del Amo, Vicente
;
Diaz, Pamela
.
JOURNAL OF ORGANIC CHEMISTRY,
2010, 75 (07)
:2407-2410

Concellon, Jose M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

Rodriguez-Solla, Humberto
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

del Amo, Vicente
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

Diaz, Pamela
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain
[17]
N-Cyanomethyl-β-chloroamines:: a convenient source of aziridinium ions
[J].
Couty, F
;
Evano, G
;
Prim, D
.
TETRAHEDRON LETTERS,
2005, 46 (13)
:2253-2257

Couty, F
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France

Evano, G
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France

Prim, D
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France
[18]
A new approach towards 2-amino-1-aryloxy-3-methoxypropanes from 1-arylmethyl-2-(bromomethyl)aziridines
[J].
D'hooghe, M
;
Waterinckx, A
;
Vanlangendonck, T
;
De Kimpe, N
.
TETRAHEDRON,
2006, 62 (10)
:2295-2303

D'hooghe, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Waterinckx, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Vanlangendonck, T
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

De Kimpe, N
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium
[19]
Ring opening of 2-(bromomethyl)-1-sulfonylaziridines towards 1,3-heteroatom substituted 2-aminopropane derivatives
[J].
D'hooghe, M
;
Rottiers, M
;
Kerkaert, I
;
De Kimpe, N
.
TETRAHEDRON,
2005, 61 (36)
:8746-8751

D'hooghe, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Rottiers, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Kerkaert, I
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

De Kimpe, N
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium
[20]
Novel synthesis of 2-aminopentanedinitriles from 2-(bromomethyl)aziridines and their transformation into 2-imino-5-methoxypyrrolidines and 5-methoxypyrrolidin-2-ones
[J].
D'hooghe, Matthias
;
Van Nieuwenhove, Andries
;
Van Brabandt, Willem
;
Rottiers, Mario
;
De Kimpe, Norbert
.
TETRAHEDRON,
2008, 64 (06)
:1064-1070

D'hooghe, Matthias
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Van Nieuwenhove, Andries
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Van Brabandt, Willem
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

Rottiers, Mario
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium

De Kimpe, Norbert
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium Univ Ghent, Fac Biosci Engn, Dept Organ Chem, B-9000 Ghent, Belgium