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Kinetic resolution of 1,2-diols through highly site- and enantioselective catalytic silylation
被引:104
作者
:
Zhao, Yu
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
Zhao, Yu
[
1
]
Mitra, Aurpon W.
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
Mitra, Aurpon W.
[
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 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Hoveyda, Amir H.
[
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 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Snapper, Marc L.
[
1
]
机构
:
[1]
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2007年
/ 46卷
/ 44期
关键词
:
asymmetric catalysis;
diols;
enantioselective synthesis;
kinetic resolution;
silylation;
D O I
:
10.1002/anie.200703650
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
(Chemical Equation Presented) Resolved to silylate: A chiral silylation catalyst is used for kinetic resolution of three classes of acyclic 1,2-diols. The catalyst differentiates, with excellent precision, between the two hydroxy groups of a substrate. The majority of the diols, obtained in high enantiomeric purity, cannot be accessed with similar stereochemical purity through catalytic asymmetric dihydroxylation. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:8471 / 8474
页数:4
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Arai K., 2007, ANGEW CHEM, V119, P973
[2]
Enantioselective desymmetrization of meso epoxides with anilines catalyzed by a niobium complex of a chiral multidentate binol derivative
Arai, Kenzo
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Arai, Kenzo
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Salter, Matthew M.
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
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Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, Shu
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2007,
46
(06)
: 955
-
957
[3]
Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope
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Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
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Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
Miller, SJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
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6502
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Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes
Denmark, SE
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Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
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Beutner, GL
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Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
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Wynn, T
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h-index:
0
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Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
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Eastgate, MD
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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
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3789
[5]
Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters
Dixon, DJ
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Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
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Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Polara, A
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Sheppard, T
[J].
ORGANIC LETTERS,
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3752
[6]
Modified guanidines as chiral superbases: the first example of asymmetric silylation of secondary alcohols
Isobe, T
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Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
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0
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Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
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[J].
CHEMICAL COMMUNICATIONS,
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(03)
: 243
-
244
[7]
Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds
Iwasaki, F
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引用数:
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h-index:
0
机构:
Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Iwasaki, F
Maki, T
论文数:
0
引用数:
0
h-index:
0
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Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Maki, T
Onomura, O
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h-index:
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Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
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Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Matsumura, Y
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2000,
65
(04)
: 996
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1002
[8]
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[9]
CATALYTIC ASYMMETRIC DIHYDROXYLATION
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SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
KOLB, HC
VANNIEUWENHZE, MS
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SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
VANNIEUWENHZE, MS
SHARPLESS, KB
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SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SHARPLESS, KB
[J].
CHEMICAL REVIEWS,
1994,
94
(08)
: 2483
-
2547
[10]
Lewis C. A., 2006, ANGEW CHEM, V118, P5744
←
1
2
3
→
共 24 条
[1]
Arai K., 2007, ANGEW CHEM, V119, P973
[2]
Enantioselective desymmetrization of meso epoxides with anilines catalyzed by a niobium complex of a chiral multidentate binol derivative
Arai, Kenzo
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Arai, Kenzo
Salter, Matthew M.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Salter, Matthew M.
Yamashita, Yasuhiro
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Yamashita, Yasuhiro
Kobayashi, Shu
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
Kobayashi, Shu
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2007,
46
(06)
: 955
-
957
[3]
Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope
Copeland, GT
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
Copeland, GT
Miller, SJ
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
Miller, SJ
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2001,
123
(27)
: 6496
-
6502
[4]
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
[5]
Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters
Dixon, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Dixon, DJ
Ley, SV
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Ley, SV
Polara, A
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
Polara, A
论文数:
引用数:
h-index:
机构:
Sheppard, T
[J].
ORGANIC LETTERS,
2001,
3
(23)
: 3749
-
3752
[6]
Modified guanidines as chiral superbases: the first example of asymmetric silylation of secondary alcohols
Isobe, T
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Isobe, T
Fukuda, K
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Fukuda, K
Araki, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Araki, Y
Ishikawa, T
论文数:
0
引用数:
0
h-index:
0
机构:
Chiba Univ, Fac Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
Ishikawa, T
[J].
CHEMICAL COMMUNICATIONS,
2001,
(03)
: 243
-
244
[7]
Chemo- and stereoselective monobenzoylation of 1,2-diols catalyzed by organotin compounds
Iwasaki, F
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Iwasaki, F
Maki, T
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Maki, T
Onomura, O
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Onomura, O
Nakashima, W
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Nakashima, W
Matsumura, Y
论文数:
0
引用数:
0
h-index:
0
机构:
Kyushu Univ, Inst Fundamental Res Organ Chem, Higashi Ku, Fukuoka 8128581, Japan
Matsumura, Y
[J].
JOURNAL OF ORGANIC CHEMISTRY,
2000,
65
(04)
: 996
-
1002
[8]
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[9]
CATALYTIC ASYMMETRIC DIHYDROXYLATION
KOLB, HC
论文数:
0
引用数:
0
h-index:
0
机构:
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
KOLB, HC
VANNIEUWENHZE, MS
论文数:
0
引用数:
0
h-index:
0
机构:
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
VANNIEUWENHZE, MS
SHARPLESS, KB
论文数:
0
引用数:
0
h-index:
0
机构:
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SCRIPPS RES INST, DEPT CHEM, LA JOLLA, CA 92037 USA
SHARPLESS, KB
[J].
CHEMICAL REVIEWS,
1994,
94
(08)
: 2483
-
2547
[10]
Lewis C. A., 2006, ANGEW CHEM, V118, P5744
←
1
2
3
→