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A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions
被引:132
作者
:
Carswell, Emma L.
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
Carswell, Emma L.
[
1
]
Snapper, Marc L.
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
Snapper, Marc L.
[
1
]
Hoveyda, Amir H.
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
Hoveyda, Amir H.
[
1
]
机构
:
[1]
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02167 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2006年
/ 45卷
/ 43期
关键词
:
asymmetric catalysis;
enantioselective synthesis;
imines;
silver;
vinylogous Mannich reactions;
D O I
:
10.1002/anie.200603496
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) Very selective but very easy: These are two of the attributes of the asymmetric vinylogous Mannich reactions presented herein. These reactions can be run on a gram scale and in undistilled THF and air (see scheme; TMS = SiMe3). All that is needed is commercially available AgOAc, a readily available amino acid derived phosphine, and a commercially available or easily prepared (one step) siloxyfuran. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7230 / 7233
页数:4
相关论文
共 28 条
[1]
Akullian L. C., 2003, ANGEW CHEM, V115, P4376
[2]
Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines
Akullian, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Akullian, LC
Snapper, ML
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Snapper, ML
Hoveyda, AH
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Hoveyda, AH
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003,
42
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: 4244
-
4247
[3]
Vinylogous Mannich reactions: Some theoretical studies on the origins of diastereoselectivity
Bur, SK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Bur, SK
Martin, SF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Martin, SF
[J].
ORGANIC LETTERS,
2000,
2
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3447
[4]
The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
Casiraghi, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
Casiraghi, G
论文数:
引用数:
h-index:
机构:
Zanardi, F
Appendino, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
Appendino, G
Rassu, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
Rassu, G
[J].
CHEMICAL REVIEWS,
2000,
100
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: 1929
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1972
[5]
Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids
Chi, Yonggui
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Chi, Yonggui
Gellman, Samuel H.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Gellman, Samuel H.
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
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: 6804
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6805
[6]
The direct catalytic asymmetric Mannich reaction
论文数:
引用数:
h-index:
机构:
Córdova, A
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(02)
: 102
-
112
[7]
Cozzi P. G., 2005, ANGEW CHEM, V117, P3666
[8]
Highly enantioselective one-pot, three-component imino-reformatsky reaction
Cozzi, PG
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
Cozzi, PG
论文数:
引用数:
h-index:
机构:
Rivalta, E
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(23)
: 3600
-
3603
[9]
Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
Beutner, GL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Beutner, GL
Wynn, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Wynn, T
Eastgate, MD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Eastgate, MD
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(11)
: 3774
-
3789
[10]
Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
Ferraris, D
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Ferraris, D
Young, B
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Young, B
Dudding, T
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Dudding, T
Lectka, T
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Lectka, T
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(18)
: 4548
-
4549
←
1
2
3
→
共 28 条
[1]
Akullian L. C., 2003, ANGEW CHEM, V115, P4376
[2]
Three-component enantioselective synthesis of propargylamines through Zr-catalyzed additions of alkyl zinc reagents to alkynylimines
Akullian, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Akullian, LC
Snapper, ML
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Snapper, ML
Hoveyda, AH
论文数:
0
引用数:
0
h-index:
0
机构:
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Hoveyda, AH
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003,
42
(35)
: 4244
-
4247
[3]
Vinylogous Mannich reactions: Some theoretical studies on the origins of diastereoselectivity
Bur, SK
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Bur, SK
Martin, SF
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Univ Texas, Dept Chem & Biochem, Austin, TX 78712 USA
Martin, SF
[J].
ORGANIC LETTERS,
2000,
2
(22)
: 3445
-
3447
[4]
The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver
Casiraghi, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
Casiraghi, G
论文数:
引用数:
h-index:
机构:
Zanardi, F
Appendino, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
Appendino, G
Rassu, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Parma, Dipartimento Farmaceut, I-43100 Parma, Italy
Rassu, G
[J].
CHEMICAL REVIEWS,
2000,
100
(06)
: 1929
-
1972
[5]
Enantioselective organocatalytic aminomethylation of aldehydes:: A role for ionic interactions and efficient access to β2-amino acids
Chi, Yonggui
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Chi, Yonggui
Gellman, Samuel H.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
Gellman, Samuel H.
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2006,
128
(21)
: 6804
-
6805
[6]
The direct catalytic asymmetric Mannich reaction
论文数:
引用数:
h-index:
机构:
Córdova, A
[J].
ACCOUNTS OF CHEMICAL RESEARCH,
2004,
37
(02)
: 102
-
112
[7]
Cozzi P. G., 2005, ANGEW CHEM, V117, P3666
[8]
Highly enantioselective one-pot, three-component imino-reformatsky reaction
Cozzi, PG
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
Cozzi, PG
论文数:
引用数:
h-index:
机构:
Rivalta, E
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005,
44
(23)
: 3600
-
3603
[9]
Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
Denmark, SE
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Denmark, SE
Beutner, GL
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Beutner, GL
Wynn, T
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Wynn, T
Eastgate, MD
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Eastgate, MD
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005,
127
(11)
: 3774
-
3789
[10]
Catalytic, enantioselective alkylation of α-imino esters using late transition metal phosphine complexes as catalysts
Ferraris, D
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Ferraris, D
Young, B
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Young, B
Dudding, T
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Dudding, T
Lectka, T
论文数:
0
引用数:
0
h-index:
0
机构:
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA
Lectka, T
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1998,
120
(18)
: 4548
-
4549
←
1
2
3
→