共 28 条
Enantioselective Bronsted acid catalyzed transfer hydrogenation: Organocatalytic reduction of imines
被引:429
作者:

Rueping, M
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机构:
Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany

Sugiono, E
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机构:
Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany

Azap, C
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机构:
Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany

Theissmann, T
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Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany

Bolte, M
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机构:
Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany
机构:
[1] Goethe Univ Frankfurt, Inst Chem & Chem Biol, D-60439 Frankfurt, Germany
关键词:
D O I:
10.1021/ol0515964
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The first enantioselective Bronsted acid catalyzed reduction of imines has been developed. This new organocatalytic transfer hydrogenation of ketimines with Hantzsch dihydropyridine as the hydrogen source offers a mild method to various chiral amines with high enantioselectivity. The stereochemistry of the chiral amines can be rationalized by a stereochemical model derived from an X-ray crystal structure of a chiral BINOL phosphate catalyst.
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页码:3781 / 3783
页数:3
相关论文
共 28 条
[1]
Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates
[J].
Akiyama, T
;
Morita, H
;
Itoh, J
;
Fuchibe, K
.
ORGANIC LETTERS,
2005, 7 (13)
:2583-2585

Akiyama, T
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Morita, H
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Itoh, J
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Fuchibe, K
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
[2]
Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
[J].
Akiyama, T
;
Itoh, J
;
Yokota, K
;
Fuchibe, K
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2004, 43 (12)
:1566-1568

Akiyama, T
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Itoh, J
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Yokota, K
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan

Fuchibe, K
论文数: 0 引用数: 0
h-index: 0
机构:
Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan Gakushuin Univ, Fac Sci, Dept Chem, Toshima Ku, Tokyo 1718588, Japan
[3]
Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts
[J].
Berkessel, A
;
Cleemann, F
;
Mukherjee, S
;
Müller, TN
;
Lex, J
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005, 44 (05)
:807-811

Berkessel, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

Cleemann, F
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

Mukherjee, S
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

Müller, TN
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

Lex, J
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
[4]
Selective hydrogenation for fine chemicals: Recent trends and new developments
[J].
Blaser, HU
;
Malan, C
;
Pugin, B
;
Spindler, F
;
Steiner, H
;
Studer, M
.
ADVANCED SYNTHESIS & CATALYSIS,
2003, 345 (1-2)
:103-151

Blaser, HU
论文数: 0 引用数: 0
h-index: 0
机构:
Solvias AG, CH-4002 Basel, Switzerland Solvias AG, CH-4002 Basel, Switzerland

Malan, C
论文数: 0 引用数: 0
h-index: 0
机构:
Solvias AG, CH-4002 Basel, Switzerland Solvias AG, CH-4002 Basel, Switzerland

Pugin, B
论文数: 0 引用数: 0
h-index: 0
机构:
Solvias AG, CH-4002 Basel, Switzerland Solvias AG, CH-4002 Basel, Switzerland

Spindler, F
论文数: 0 引用数: 0
h-index: 0
机构:
Solvias AG, CH-4002 Basel, Switzerland Solvias AG, CH-4002 Basel, Switzerland

Steiner, H
论文数: 0 引用数: 0
h-index: 0
机构:
Solvias AG, CH-4002 Basel, Switzerland Solvias AG, CH-4002 Basel, Switzerland

Studer, M
论文数: 0 引用数: 0
h-index: 0
机构:
Solvias AG, CH-4002 Basel, Switzerland Solvias AG, CH-4002 Basel, Switzerland
[5]
Chemo- and enantioselective hydrosilylation of carbonyl and imino groups. An emphasis on non-traditional catalyst systems
[J].
Carpentier, JF
;
Bette, V
.
CURRENT ORGANIC CHEMISTRY,
2002, 6 (10)
:913-936

Carpentier, JF
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rennes 1, Lab Organomet & Catalyse, UMR 6509, CNRS, F-35042 Rennes, France Univ Rennes 1, Lab Organomet & Catalyse, UMR 6509, CNRS, F-35042 Rennes, France

Bette, V
论文数: 0 引用数: 0
h-index: 0
机构: Univ Rennes 1, Lab Organomet & Catalyse, UMR 6509, CNRS, F-35042 Rennes, France
[6]
Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst
[J].
Huang, Y
;
Unni, AK
;
Thadani, AN
;
Rawal, VH
.
NATURE,
2003, 424 (6945)
:146-146

Huang, Y
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Chicago, Dept Chem, Chicago, IL 60637 USA Univ Chicago, Dept Chem, Chicago, IL 60637 USA

Unni, AK
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Chicago, Dept Chem, Chicago, IL 60637 USA Univ Chicago, Dept Chem, Chicago, IL 60637 USA

Thadani, AN
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Chicago, Dept Chem, Chicago, IL 60637 USA Univ Chicago, Dept Chem, Chicago, IL 60637 USA

Rawal, VH
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Chicago, Dept Chem, Chicago, IL 60637 USA Univ Chicago, Dept Chem, Chicago, IL 60637 USA
[7]
Highly enantioselective hydrogen-transfer reductive amination: Catalytic asymmetric synthesis of primary amines
[J].
Kadyrov, R
;
Riermeier, TH
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2003, 42 (44)
:5472-5474

Kadyrov, R
论文数: 0 引用数: 0
h-index: 0
机构:
Degussa AG, Projekthaus Katalyse, D-65926 Frankfurt, Germany Degussa AG, Projekthaus Katalyse, D-65926 Frankfurt, Germany

Riermeier, TH
论文数: 0 引用数: 0
h-index: 0
机构:
Degussa AG, Projekthaus Katalyse, D-65926 Frankfurt, Germany Degussa AG, Projekthaus Katalyse, D-65926 Frankfurt, Germany
[8]
Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane
[J].
Malkov, AV
;
Mariani, A
;
MacDougall, KN
;
Kocovsky, P
.
ORGANIC LETTERS,
2004, 6 (13)
:2253-2256

Malkov, AV
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

Mariani, A
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

MacDougall, KN
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland

Kocovsky, P
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland Univ Glasgow, Dept Chem, Glasgow G12 8QQ, Lanark, Scotland
[9]
Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Bronsted acids
[J].
McDougal, NT
;
Schaus, SE
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2003, 125 (40)
:12094-12095

McDougal, NT
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA

Schaus, SE
论文数: 0 引用数: 0
h-index: 0
机构:
Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA
[10]
Chiral proton catalysis: A catalytic enantioselective direct aza-Henry reaction
[J].
Nugent, BM
;
Yoder, RA
;
Johnston, JN
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2004, 126 (11)
:3418-3419

Nugent, BM
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

Yoder, RA
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA

Johnston, JN
论文数: 0 引用数: 0
h-index: 0
机构:
Indiana Univ, Dept Chem, Bloomington, IN 47405 USA Indiana Univ, Dept Chem, Bloomington, IN 47405 USA