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Trimethylsilyl Trifluoromethanesulfonate-Accelerated Addition of Catalytically Generated Zinc Acetylides to Aldehydes
被引:31
作者
:
Downey, C. Wade
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Downey, C. Wade
[
1
]
Mahoney, Brian D.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Mahoney, Brian D.
[
1
]
Lipari, Vincent R.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Lipari, Vincent R.
[
1
]
机构
:
[1]
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
来源
:
JOURNAL OF ORGANIC CHEMISTRY
|
2009年
/ 74卷
/ 07期
关键词
:
PROPARGYLIC ALCOHOLS;
TERMINAL ALKYNES;
ENANTIOSELECTIVE SYNTHESIS;
ACETYLENES;
KETONES;
FACILE;
TMSOTF;
D O I
:
10.1021/jo900102w
中图分类号
:
O62 [有机化学];
学科分类号
:
070303 ;
081704 ;
摘要
:
In the presence of TMSOTf, a wide variety of terminal acetylenes add rapidly and efficiently to aldehydes via a catalytically generated zinc acetylide. In the absence of TMSOTf, no reaction is observed under otherwise identical conditions.
引用
收藏
页码:2904 / 2906
页数:3
相关论文
共 16 条
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A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
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0
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Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Anand, NK
Carreira, EM
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0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(39)
: 9687
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9688
[2]
Enantioselective addition of terminal alkynes to aldehydes catalyzed by a Cu(I)-TRAP complex
Asano, Yohsuke
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0
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Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
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Asano, Yohsuke
Hara, Kenji
论文数:
0
引用数:
0
h-index:
0
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Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hara, Kenji
Ito, Hajime
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引用数:
0
h-index:
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Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Ito, Hajime
论文数:
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Sawamura, Masaya
[J].
ORGANIC LETTERS,
2007,
9
(20)
: 3901
-
3904
[3]
Me2Zn-mediated addition of acetylenes to aldehydes and ketones
Cozzi, PG
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0
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0
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Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Cozzi, PG
Rudolph, J
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Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
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Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
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Norrby, PO
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0
h-index:
0
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Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Norrby, PO
Tomasini, C
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0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Tomasini, C
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2005,
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(14)
: 5733
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[4]
One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf
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Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
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Johnson, Miles W.
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Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
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Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
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[J].
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A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf
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Univ Richmond, Dept Chem, Richmond, VA 23173 USA
Univ Richmond, Dept Chem, Richmond, VA 23173 USA
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Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
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[J].
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Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes
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ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
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Fässler, R
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ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
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Carreira, EM
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ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
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[J].
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Highly enantioselective synthesis of γ-hydroxy-α,β-acetylenic esters by asymmetric alkyne addition to aldehydes
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Univ Tennessee, Dept Chem, Knoxville, TN 37006 USA
Ju, YH
[J].
ORGANIC LETTERS,
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: 3929
-
3931
[10]
Lee KY, 2005, B KOR CHEM SOC, V26, P1617
←
1
2
→
共 16 条
[1]
A simple, mild, catalytic, enantioselective addition of terminal acetylenes to aldehydes
Anand, NK
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Anand, NK
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Swiss Fed Inst Technol, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(39)
: 9687
-
9688
[2]
Enantioselective addition of terminal alkynes to aldehydes catalyzed by a Cu(I)-TRAP complex
Asano, Yohsuke
论文数:
0
引用数:
0
h-index:
0
机构:
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Asano, Yohsuke
Hara, Kenji
论文数:
0
引用数:
0
h-index:
0
机构:
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hara, Kenji
Ito, Hajime
论文数:
0
引用数:
0
h-index:
0
机构:
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
Ito, Hajime
论文数:
引用数:
h-index:
机构:
Sawamura, Masaya
[J].
ORGANIC LETTERS,
2007,
9
(20)
: 3901
-
3904
[3]
Me2Zn-mediated addition of acetylenes to aldehydes and ketones
Cozzi, PG
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Cozzi, PG
Rudolph, J
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Rudolph, J
Bolm, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Bolm, C
Norrby, PO
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Norrby, PO
Tomasini, C
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Bologna, Dipartimento Chim G Ciamician, Alma Mater Studiorum, I-40126 Bologna, Italy
Tomasini, C
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2005,
70
(14)
: 5733
-
5736
[4]
One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf
Downey, C. Wade
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Downey, C. Wade
Johnson, Miles W.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Johnson, Miles W.
Tracy, Kathryn J.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Univ Richmond, Gottwald Ctr Sci, Richmond, VA 23173 USA
Tracy, Kathryn J.
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2008,
73
(08)
: 3299
-
3302
[5]
A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf
Downey, C. Wade
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Dept Chem, Richmond, VA 23173 USA
Univ Richmond, Dept Chem, Richmond, VA 23173 USA
Downey, C. Wade
Johnson, Miles W.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Richmond, Dept Chem, Richmond, VA 23173 USA
Univ Richmond, Dept Chem, Richmond, VA 23173 USA
Johnson, Miles W.
[J].
TETRAHEDRON LETTERS,
2007,
48
(20)
: 3559
-
3562
[6]
Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement
Engel, Douglas A.
论文数:
0
引用数:
0
h-index:
0
机构:
Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
Engel, Douglas A.
Dudley, Gregory B.
论文数:
0
引用数:
0
h-index:
0
机构:
Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
Dudley, Gregory B.
[J].
ORGANIC LETTERS,
2006,
8
(18)
: 4027
-
4029
[7]
Facile enantioselective synthesis of propargylic alcohols by direct addition of terminal alkynes to aldehydes
Frantz, DE
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Frantz, DE
Fässler, R
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Fässler, R
Carreira, EM
论文数:
0
引用数:
0
h-index:
0
机构:
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland
Carreira, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2000,
122
(08)
: 1806
-
1807
[8]
Highly enantioselective synthesis of γ-hydroxy-α,β-acetylenic esters by asymmetric alkyne addition to aldehydes
Gao, G
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Gao, G
Wang, Q
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Wang, Q
Yu, XQ
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Yu, XQ
Xie, RG
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Xie, RG
Pu, L
论文数:
0
引用数:
0
h-index:
0
机构:
Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
Pu, L
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2006,
45
(01)
: 122
-
125
[9]
A new halopropargylation of alkynes promoted by boron trihalides.: Highly stereo- and regioselective syntheses of substituted (Z)-1-halo-1,4-enyne derivatives
Kabalka, GW
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tennessee, Dept Chem, Knoxville, TN 37006 USA
Univ Tennessee, Dept Chem, Knoxville, TN 37006 USA
Kabalka, GW
Wu, ZZ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tennessee, Dept Chem, Knoxville, TN 37006 USA
Wu, ZZ
Ju, YH
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tennessee, Dept Chem, Knoxville, TN 37006 USA
Ju, YH
[J].
ORGANIC LETTERS,
2004,
6
(22)
: 3929
-
3931
[10]
Lee KY, 2005, B KOR CHEM SOC, V26, P1617
←
1
2
→