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Catalytic enantioselective aldol additions of α-isothiocyanato imides to α-ketoesters
被引:39
作者
:
Vecchione, Matthew K.
论文数:
0
引用数:
0
h-index:
0
机构:
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
Vecchione, Matthew K.
[
1
]
Li, Le
论文数:
0
引用数:
0
h-index:
0
机构:
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
Li, Le
[
1
]
Seidel, Daniel
论文数:
0
引用数:
0
h-index:
0
机构:
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
Seidel, Daniel
[
1
]
机构
:
[1]
Rutgers State Univ, Dept Chem & Chem Biol, Piscataway, NJ 08854 USA
来源
:
CHEMICAL COMMUNICATIONS
|
2010年
/ 46卷
/ 25期
关键词
:
AMINO ACID-DERIVATIVES;
QUATERNARY AMMONIUM-SALTS;
ASYMMETRIC-SYNTHESIS;
CINCHONA ALKALOIDS;
NONADJACENT STEREOCENTERS;
CONJUGATE ADDITION;
EFFICIENT APPROACH;
CYCLIC-PEPTIDES;
BOND DONORS;
SCHIFF-BASE;
D O I
:
10.1039/c0cc00556h
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
A readily available bifunctional thiourea catalyst promotes aldol additions of alpha-isothiocyanato imides to alpha-ketoesters under mild reaction conditions to form beta-hydroxy-alpha-amino acid derivatives with high levels of enantioselectivity.
引用
收藏
页码:4604 / 4606
页数:3
相关论文
共 72 条
[1]
Enantioselective organocatalyzed Henry reaction with fluoromethyl ketones
[J].
Bandini, Marco
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0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Bandini, Marco
;
Sinisi, Riccardo
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0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Sinisi, Riccardo
;
Umani-Ronchi, Achille
论文数:
0
引用数:
0
h-index:
0
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Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Umani-Ronchi, Achille
.
CHEMICAL COMMUNICATIONS,
2008,
(36)
:4360
-4362
[2]
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3]
Organocatalysis-after the gold rush
[J].
Bertelsen, Soren
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Bertelsen, Soren
;
Jorgensen, Karl Anker
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0
h-index:
0
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Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Jorgensen, Karl Anker
.
CHEMICAL SOCIETY REVIEWS,
2009,
38
(08)
:2178
-2189
[4]
TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN
[J].
BOGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla
BOGER, DL
;
PATANE, MA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla
PATANE, MA
;
ZHOU, JC
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla
ZHOU, JC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1994,
116
(19)
:8544
-8556
[5]
TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .1. SYNTHESIS AND DNA-BINDING PROPERTIES OF THE EXTENDED C-TERMINUS - TRIPEPTIDE-S, TETRAPEPTIDE-S, PENTAPEPTIDE-S, AND RELATED AGENTS
[J].
BOGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
BOGER, DL
;
COLLETTI, SL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
COLLETTI, SL
;
HONDA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
HONDA, T
;
MENEZES, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
MENEZES, RF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1994,
116
(13)
:5607
-5618
[6]
Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine
[J].
Bui, Tommy
论文数:
0
引用数:
0
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0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Bui, Tommy
;
Syed, Salahuddin
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0
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0
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0
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Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Syed, Salahuddin
;
Barbas, Carlos F., III
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0
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0
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0
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Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Barbas, Carlos F., III
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2009,
131
(25)
:8758
-+
[7]
Preparation of α-amino-carboxylic acid derivatives via diastereoselective reactions of glycine enolate equivalents
[J].
Caddick, S
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0
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Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Caddick, S
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Parr, NJ
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0
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Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Parr, NJ
;
Pritchard, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Pritchard, MC
.
TETRAHEDRON,
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57
(30)
:6615
-6626
[8]
Organocatalysis mediated by (thio)urea derivatives
[J].
Connon, Stephen J.
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0
引用数:
0
h-index:
0
机构:
Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
Connon, Stephen J.
.
CHEMISTRY-A EUROPEAN JOURNAL,
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12
(21)
:5418
-5427
[9]
Expedient synthesis of threo-β-hydroxy-α-amino acid derivatives:: Phenylalanine, tyrosine, histidine, and tryptophan
[J].
Crich, David
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Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
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[10]
Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids
[J].
Cutting, Gary A.
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John, Matthew P.
;
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h-index:
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Kociok-Koehn, Gabriele
;
Willis, Michael C.
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引用数:
0
h-index:
0
机构:
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Willis, Michael C.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007,
129
(35)
:10632
-+
←
1
2
3
4
5
6
7
8
→
共 72 条
[1]
Enantioselective organocatalyzed Henry reaction with fluoromethyl ketones
[J].
Bandini, Marco
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Bandini, Marco
;
Sinisi, Riccardo
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Sinisi, Riccardo
;
Umani-Ronchi, Achille
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy
Umani-Ronchi, Achille
.
CHEMICAL COMMUNICATIONS,
2008,
(36)
:4360
-4362
[2]
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3]
Organocatalysis-after the gold rush
[J].
Bertelsen, Soren
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Bertelsen, Soren
;
Jorgensen, Karl Anker
论文数:
0
引用数:
0
h-index:
0
机构:
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark
Jorgensen, Karl Anker
.
CHEMICAL SOCIETY REVIEWS,
2009,
38
(08)
:2178
-2189
[4]
TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN
[J].
BOGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla
BOGER, DL
;
PATANE, MA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla
PATANE, MA
;
ZHOU, JC
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla
ZHOU, JC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1994,
116
(19)
:8544
-8556
[5]
TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .1. SYNTHESIS AND DNA-BINDING PROPERTIES OF THE EXTENDED C-TERMINUS - TRIPEPTIDE-S, TETRAPEPTIDE-S, PENTAPEPTIDE-S, AND RELATED AGENTS
[J].
BOGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
BOGER, DL
;
COLLETTI, SL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
COLLETTI, SL
;
HONDA, T
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
HONDA, T
;
MENEZES, RF
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037
MENEZES, RF
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1994,
116
(13)
:5607
-5618
[6]
Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine
[J].
Bui, Tommy
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Bui, Tommy
;
Syed, Salahuddin
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Syed, Salahuddin
;
Barbas, Carlos F., III
论文数:
0
引用数:
0
h-index:
0
机构:
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
Barbas, Carlos F., III
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2009,
131
(25)
:8758
-+
[7]
Preparation of α-amino-carboxylic acid derivatives via diastereoselective reactions of glycine enolate equivalents
[J].
Caddick, S
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Caddick, S
;
Parr, NJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Parr, NJ
;
Pritchard, MC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
Pritchard, MC
.
TETRAHEDRON,
2001,
57
(30)
:6615
-6626
[8]
Organocatalysis mediated by (thio)urea derivatives
[J].
Connon, Stephen J.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
Univ Dublin Trinity Coll, Sch Chem, Ctr Synth & Chem Biol, Dublin 2, Ireland
Connon, Stephen J.
.
CHEMISTRY-A EUROPEAN JOURNAL,
2006,
12
(21)
:5418
-5427
[9]
Expedient synthesis of threo-β-hydroxy-α-amino acid derivatives:: Phenylalanine, tyrosine, histidine, and tryptophan
[J].
Crich, David
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Crich, David
;
Banerjee, Abhisek
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Univ Illinois, Dept Chem, Chicago, IL 60607 USA
Banerjee, Abhisek
.
JOURNAL OF ORGANIC CHEMISTRY,
2006,
71
(18)
:7106
-7109
[10]
Direct catalytic enantioselective mannich reactions:: Synthesis of protected anti-α,β-diamino acids
[J].
Cutting, Gary A.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Cutting, Gary A.
;
Stainforth, Nikki E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Stainforth, Nikki E.
;
John, Matthew P.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
John, Matthew P.
;
Kociok-Koehn, Gabriele
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Kociok-Koehn, Gabriele
;
Willis, Michael C.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
Willis, Michael C.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007,
129
(35)
:10632
-+
←
1
2
3
4
5
6
7
8
→