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Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes
被引:73
作者
:
Nelson, SG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Nelson, SG
[
1
]
Zhu, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Zhu, C
[
1
]
Shen, XQ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Shen, XQ
[
1
]
机构
:
[1]
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2004年
/ 126卷
/ 01期
关键词
:
D O I
:
10.1021/ja0391208
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Catalytic asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted β-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal′s dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions. Copyright © 2004 American Chemical Society.
引用
收藏
页码:14 / 15
页数:2
相关论文
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First total synthesis of a natural product containing a chiral, β-diketone:: Synthesis and stereochemical reassignment of siphonarienedione and siphonarienolone
Calter, MA
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Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Calter, MA
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0
h-index:
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Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Liao, WS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(44)
: 13127
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[2]
Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones
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0
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Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Cortez, GS
Tennyson, RL
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Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Tennyson, RL
Romo, D
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0
h-index:
0
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Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Romo, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(32)
: 7945
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7946
[3]
Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones
Evans, DA
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0
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0
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Tedrow, JS
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Tedrow, JS
Shaw, JT
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
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Downey, CW
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
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[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(03)
: 392
-
393
[4]
C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes
Evans, DA
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
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Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Janey, JM
[J].
ORGANIC LETTERS,
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[5]
Catalytic asymmetric homo-aldol reaction of pyruvate - a chiral Lewis acid catalyst that mimics aldolase enzymes
Juhl, K
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Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Juhl, K
Gathergood, N
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Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Gathergood, N
Jorgensen, KA
论文数:
0
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0
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0
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Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Jorgensen, KA
[J].
CHEMICAL COMMUNICATIONS,
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(22)
: 2211
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[6]
Lewis acidity expressed in neutral electron-rich aluminum(III) complexes: An example of ligand-defined catalysis
Nelson, SG
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Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
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Kim, BK
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0
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Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Kim, BK
Peelen, TJ
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0
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0
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Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Peelen, TJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(38)
: 9318
-
9319
[7]
SN2 ring opening of β-lactones:: An alternative to catalytic asymmetric conjugate additions
Nelson, SG
论文数:
0
引用数:
0
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0
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Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Nelson, SG
Wan, ZH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Wan, ZH
Stan, MA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Stan, MA
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2002,
67
(14)
: 4680
-
4683
[8]
Nelson SG, 2000, ANGEW CHEM INT EDIT, V39, P1323, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1323::AID-ANIE1323>3.0.CO
[9]
2-X
[10]
Mechanistic alternatives in Lewis acid-catalyzed acyl halide-aldehyde cyclocondensations
Nelson, SG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Nelson, SG
Peelen, TJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Peelen, TJ
Wan, ZH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Wan, ZH
[J].
TETRAHEDRON LETTERS,
1999,
40
(36)
: 6541
-
6543
←
1
2
3
→
共 21 条
[1]
First total synthesis of a natural product containing a chiral, β-diketone:: Synthesis and stereochemical reassignment of siphonarienedione and siphonarienolone
Calter, MA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Calter, MA
Liao, WS
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Univ Rochester, Dept Chem, Rochester, NY 14627 USA
Liao, WS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(44)
: 13127
-
13129
[2]
Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones
Cortez, GS
论文数:
0
引用数:
0
h-index:
0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Cortez, GS
Tennyson, RL
论文数:
0
引用数:
0
h-index:
0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Tennyson, RL
Romo, D
论文数:
0
引用数:
0
h-index:
0
机构:
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA
Romo, D
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(32)
: 7945
-
7946
[3]
Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Tedrow, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Tedrow, JS
Shaw, JT
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Shaw, JT
Downey, CW
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Downey, CW
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(03)
: 392
-
393
[4]
C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic, enantioselective cycloadditions of silyl ketenes
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Evans, DA
Janey, JM
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
Janey, JM
[J].
ORGANIC LETTERS,
2001,
3
(13)
: 2125
-
2128
[5]
Catalytic asymmetric homo-aldol reaction of pyruvate - a chiral Lewis acid catalyst that mimics aldolase enzymes
Juhl, K
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Juhl, K
Gathergood, N
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Gathergood, N
Jorgensen, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Met Catalysed React, DK-8000 Aarhus C, Denmark
Jorgensen, KA
[J].
CHEMICAL COMMUNICATIONS,
2000,
(22)
: 2211
-
2212
[6]
Lewis acidity expressed in neutral electron-rich aluminum(III) complexes: An example of ligand-defined catalysis
Nelson, SG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Nelson, SG
Kim, BK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Kim, BK
Peelen, TJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Peelen, TJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(38)
: 9318
-
9319
[7]
SN2 ring opening of β-lactones:: An alternative to catalytic asymmetric conjugate additions
Nelson, SG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Nelson, SG
Wan, ZH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Wan, ZH
Stan, MA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
Stan, MA
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2002,
67
(14)
: 4680
-
4683
[8]
Nelson SG, 2000, ANGEW CHEM INT EDIT, V39, P1323, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1323::AID-ANIE1323>3.0.CO
[9]
2-X
[10]
Mechanistic alternatives in Lewis acid-catalyzed acyl halide-aldehyde cyclocondensations
Nelson, SG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Nelson, SG
Peelen, TJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Peelen, TJ
Wan, ZH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15206 USA
Wan, ZH
[J].
TETRAHEDRON LETTERS,
1999,
40
(36)
: 6541
-
6543
←
1
2
3
→