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An easy approach to optically active α-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates
被引:103
作者
:
Bernardi, L
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Ctr Catalysis, Dept Chem, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
Bernardi, L
Zhuang, W
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Ctr Catalysis, Dept Chem, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
Zhuang, W
Jorgensen, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Ctr Catalysis, Dept Chem, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
Aarhus Univ, Ctr Catalysis, Dept Chem, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
Jorgensen, KA
[
1
]
机构
:
[1]
Aarhus Univ, Ctr Catalysis, Dept Chem, Danish Natl Res Fdn, DK-8000 Aarhus, Denmark
[2]
Fac Chim Ind, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2005年
/ 127卷
/ 16期
关键词
:
D O I
:
10.1021/ja050989v
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
A catalytic direct enantioselective electrophilic amination of β-keto phosphonates has been developed applying chiral bisoxazoline-zinc(II) complexes as the catalyst. The reaction proceeds well for both acyclic and cyclic substrates in high yields and with up to 98% ee using azodicarboxylates as the nitrogen source. The scope of the reaction is, for example, the further transformation to optically active β-hydroxy-α-amino phosphonates with very high stereoselection. Copyright © 2005 American Chemical Society.
引用
收藏
页码:5772 / 5773
页数:2
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PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS
ALLEN, JG
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ALLEN, JG
ATHERTON, FR
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HASSALL, CH
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HOLMES, SW
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HOLMES, SW
LAMBERT, RW
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0
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0
LAMBERT, RW
NISBET, LJ
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NISBET, LJ
RINGROSE, PS
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RINGROSE, PS
[J].
NATURE,
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RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND
ALLEN, MC
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0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
ALLEN, MC
FUHRER, W
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0
引用数:
0
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CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
FUHRER, W
TUCK, B
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0
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h-index:
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CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
TUCK, B
WADE, R
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引用数:
0
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CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
WADE, R
WOOD, JM
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0
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CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
WOOD, JM
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JOURNAL OF MEDICINAL CHEMISTRY,
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SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID
ATHERTON, FR
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0
引用数:
0
h-index:
0
机构:
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ATHERTON, FR
HASSALL, CH
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0
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0
h-index:
0
机构:
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
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LAMBERT, RW
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0
引用数:
0
h-index:
0
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ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
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JOURNAL OF MEDICINAL CHEMISTRY,
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ALPHA-AMINOPHOSPHONATE DERIVATIVES AS NUCLEOPHILES IN DIASTEREOSELECTIVE AND ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS
BALDWIN, IC
论文数:
0
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0
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0
机构:
LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
BALDWIN, IC
WILLIAMS, JMJ
论文数:
0
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0
h-index:
0
机构:
LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
WILLIAMS, JMJ
BECKETT, RP
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0
机构:
LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
BECKETT, RP
[J].
TETRAHEDRON-ASYMMETRY,
1995,
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: 679
-
682
[5]
BAYER AG, 1992, CHEM ABSTR, V117
[6]
Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids
Bernardi, L
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Bernardi, L
Jorgensen, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Jorgensen, KA
[J].
CHEMICAL COMMUNICATIONS,
2005,
(10)
: 1324
-
1326
[7]
Sulfinimine-mediated asymmetric synthesis of β-hydroxy α-amino phosphonates
Davis, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Davis, FA
Prasad, KR
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Prasad, KR
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
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7253
[8]
DENMARK S, 1995, TETRAHEDRON, V48, P2191
[9]
ERLIK E, 2004, TETRAHEDRON, V60, P8747
[10]
Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes
Evans, DA
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0
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机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
Scheidt, KA
论文数:
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机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Scheidt, KA
Johnston, JN
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0
引用数:
0
h-index:
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机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Johnston, JN
Willis, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Willis, MC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(19)
: 4480
-
4491
←
1
2
3
4
→
共 40 条
[1]
PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS
ALLEN, JG
论文数:
0
引用数:
0
h-index:
0
ALLEN, JG
ATHERTON, FR
论文数:
0
引用数:
0
h-index:
0
ATHERTON, FR
HALL, MJ
论文数:
0
引用数:
0
h-index:
0
HALL, MJ
HASSALL, CH
论文数:
0
引用数:
0
h-index:
0
HASSALL, CH
HOLMES, SW
论文数:
0
引用数:
0
h-index:
0
HOLMES, SW
LAMBERT, RW
论文数:
0
引用数:
0
h-index:
0
LAMBERT, RW
NISBET, LJ
论文数:
0
引用数:
0
h-index:
0
NISBET, LJ
RINGROSE, PS
论文数:
0
引用数:
0
h-index:
0
RINGROSE, PS
[J].
NATURE,
1978,
272
(5648)
: 56
-
58
[2]
RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND
ALLEN, MC
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
ALLEN, MC
FUHRER, W
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
FUHRER, W
TUCK, B
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
TUCK, B
WADE, R
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
WADE, R
WOOD, JM
论文数:
0
引用数:
0
h-index:
0
机构:
CIBA GEIGY AG,DIV PHARMACEUT,RES DEPT,CH-4002 BASEL,SWITZERLAND
WOOD, JM
[J].
JOURNAL OF MEDICINAL CHEMISTRY,
1989,
32
(07)
: 1652
-
1661
[3]
SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID
ATHERTON, FR
论文数:
0
引用数:
0
h-index:
0
机构:
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ATHERTON, FR
HASSALL, CH
论文数:
0
引用数:
0
h-index:
0
机构:
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
HASSALL, CH
LAMBERT, RW
论文数:
0
引用数:
0
h-index:
0
机构:
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
ROCHE PROD LTD,DEPT CHEM,WELWYN GARDEN CIT AL7 3AY,HERTS,ENGLAND
LAMBERT, RW
[J].
JOURNAL OF MEDICINAL CHEMISTRY,
1986,
29
(01)
: 29
-
40
[4]
ALPHA-AMINOPHOSPHONATE DERIVATIVES AS NUCLEOPHILES IN DIASTEREOSELECTIVE AND ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS
BALDWIN, IC
论文数:
0
引用数:
0
h-index:
0
机构:
LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
BALDWIN, IC
WILLIAMS, JMJ
论文数:
0
引用数:
0
h-index:
0
机构:
LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
WILLIAMS, JMJ
BECKETT, RP
论文数:
0
引用数:
0
h-index:
0
机构:
LOUGHBOROUGH UNIV TECHNOL,DEPT CHEM,LOUGHBOROUGH LE11 3TU,LEICS,ENGLAND
BECKETT, RP
[J].
TETRAHEDRON-ASYMMETRY,
1995,
6
(03)
: 679
-
682
[5]
BAYER AG, 1992, CHEM ABSTR, V117
[6]
Enantioselective chlorination and fluorination of β-keto phosphonates catalyzed by chiral Lewis acids
Bernardi, L
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Bernardi, L
Jorgensen, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
Jorgensen, KA
[J].
CHEMICAL COMMUNICATIONS,
2005,
(10)
: 1324
-
1326
[7]
Sulfinimine-mediated asymmetric synthesis of β-hydroxy α-amino phosphonates
Davis, FA
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Davis, FA
Prasad, KR
论文数:
0
引用数:
0
h-index:
0
机构:
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Temple Univ, Dept Chem, Philadelphia, PA 19122 USA
Prasad, KR
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2003,
68
(19)
: 7249
-
7253
[8]
DENMARK S, 1995, TETRAHEDRON, V48, P2191
[9]
ERLIK E, 2004, TETRAHEDRON, V60, P8747
[10]
Enantioselective and diastereoselective mukaiyama-Michael reactions catalyzed by bis(oxazoline) Copper(II) complexes
Evans, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Evans, DA
Scheidt, KA
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Scheidt, KA
Johnston, JN
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Johnston, JN
Willis, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
Willis, MC
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(19)
: 4480
-
4491
←
1
2
3
4
→