共 42 条
Diastereoselective synthesis of pyrrolidine derivatives via a one-pot nitro-Mannich/hydroamination cascade using base and gold catalysis
被引:19
作者:

Duris, Andrej
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机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Barber, David M.
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h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Sanganee, Hitesh J.
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机构:
AstraZeneca R&D, New Opportun iMed, Alderley Pk SK10 4GT, Cheshire, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Dixon, Darren J.
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机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
机构:
[1] Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
[2] AstraZeneca R&D, New Opportun iMed, Alderley Pk SK10 4GT, Cheshire, England
基金:
英国工程与自然科学研究理事会;
关键词:
INTRAMOLECULAR HYDROAMINATION;
INTERMOLECULAR HYDROAMINATION;
ENANTIOSELECTIVE SYNTHESIS;
STEREOSELECTIVE-SYNTHESIS;
AZOMETHINE YLIDES;
ATOM ECONOMY;
ALLENES;
(-)-NAKADOMARIN;
REPLACEMENT;
METATHESIS;
D O I:
10.1039/c3cc40729b
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
An efficient one-pot nitro-Mannich/hydroamination cascade reaction for the synthesis of substituted pyrrolidines bearing three stereocentres is reported. Proceeding under the control of a combination of base and gold(I) catalysts, the cascade reaction affords the pyrrolidine products in high yields with good to excellent diastereoselectivities.
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页码:2777 / 2779
页数:3
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共 42 条
[11]
Carbon-heteroatom bond formation catalysed by organometallic complexes
[J].
Hartwig, John F.
.
NATURE,
2008, 455 (7211)
:314-322

Hartwig, John F.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Illinois, Dept Chem, Urbana, IL 61801 USA Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[12]
Gold(I)-catalysed synthesis of cyclic sulfamidates by intramolecular allene hydroamination
[J].
Higginbotham, Mari C. M.
;
Bebbington, Magnus W. P.
.
CHEMICAL COMMUNICATIONS,
2012, 48 (61)
:7565-7567

Higginbotham, Mari C. M.
论文数: 0 引用数: 0
h-index: 0
机构:
Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4AS, Midlothian, Scotland Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4AS, Midlothian, Scotland

Bebbington, Magnus W. P.
论文数: 0 引用数: 0
h-index: 0
机构:
Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4AS, Midlothian, Scotland Heriot Watt Univ, Inst Chem Sci, Edinburgh EH14 4AS, Midlothian, Scotland
[13]
Cyclic imine nitro-Mannich/lactamization cascades: A direct stereoselective synthesis of multicyclic piperidinone derivatives
[J].
Jakubec, Pavol
;
Helliwell, Madeleine
;
Dixon, Darren J.
.
ORGANIC LETTERS,
2008, 10 (19)
:4267-4270

Jakubec, Pavol
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

Helliwell, Madeleine
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
[14]
Total Synthesis of Manzamine A and Related Alkaloids
[J].
Jakubec, Pavol
;
Hawkins, Alison
;
Felzmann, Wolfgang
;
Dixon, Darren J.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2012, 134 (42)
:17482-17485

Jakubec, Pavol
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

Hawkins, Alison
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

Felzmann, Wolfgang
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[15]
Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles
[J].
Jakubec, Pavol
;
Cockfield, Dane M.
;
Helliwell, Madeleine
;
Raftery, James
;
Dixon, Darren J.
.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,
2012, 8
:567-578

Jakubec, Pavol
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Cockfield, Dane M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Helliwell, Madeleine
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Raftery, James
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
[16]
Total synthesis of (-)-nakadomarin A: alkyne ring-closing metathesis
[J].
Jakubec, Pavol
;
Kyle, Andrew F.
;
Calleja, Jonas
;
Dixon, Darren J.
.
TETRAHEDRON LETTERS,
2011, 52 (46)
:6094-6097

Jakubec, Pavol
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Kyle, Andrew F.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Calleja, Jonas
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England
[17]
Intermolecular hydroamination of allenes with N-unsubstituted carbamates catalyzed by a gold(I) N-heterocyclic carbene complex
[J].
Kinder, Robert E.
;
Zhang, Zhibin
;
Widenhoefer, Ross A.
.
ORGANIC LETTERS,
2008, 10 (14)
:3157-3159

Kinder, Robert E.
论文数: 0 引用数: 0
h-index: 0
机构:
Duke Univ, French Family Sci Ctr, Durham, NC 27708 USA Duke Univ, French Family Sci Ctr, Durham, NC 27708 USA

Zhang, Zhibin
论文数: 0 引用数: 0
h-index: 0
机构:
Duke Univ, French Family Sci Ctr, Durham, NC 27708 USA Duke Univ, French Family Sci Ctr, Durham, NC 27708 USA

Widenhoefer, Ross A.
论文数: 0 引用数: 0
h-index: 0
机构:
Duke Univ, French Family Sci Ctr, Durham, NC 27708 USA Duke Univ, French Family Sci Ctr, Durham, NC 27708 USA
[18]
Catalytic Enantioselective Formation of C-C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
[J].
Kobayashi, Shu
;
Mori, Yuichiro
;
Fossey, John S.
;
Salter, Matthew M.
.
CHEMICAL REVIEWS,
2011, 111 (04)
:2626-2704

Kobayashi, Shu
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

Mori, Yuichiro
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

Fossey, John S.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

Salter, Matthew M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan
[19]
Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes: A Powerful Access to Carbo- and Heterocycles
[J].
Krause, Norbert
;
Winter, Christian
.
CHEMICAL REVIEWS,
2011, 111 (03)
:1994-2009

Krause, Norbert
论文数: 0 引用数: 0
h-index: 0
机构:
Dortmund Univ Technol, D-44227 Dortmund, Germany Dortmund Univ Technol, D-44227 Dortmund, Germany

Winter, Christian
论文数: 0 引用数: 0
h-index: 0
机构:
Dortmund Univ Technol, D-44227 Dortmund, Germany Dortmund Univ Technol, D-44227 Dortmund, Germany
[20]
Total synthesis of (-)-nakadomarin A
[J].
Kyle, Andrew F.
;
Jakubec, Pavol
;
Cockfield, Dane M.
;
Cleator, Ed
;
Skidmore, John
;
Dixon, Darren J.
.
CHEMICAL COMMUNICATIONS,
2011, 47 (36)
:10037-10039

Kyle, Andrew F.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Jakubec, Pavol
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Cockfield, Dane M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Manchester, Sch Chem, Manchester, Lancs, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Cleator, Ed
论文数: 0 引用数: 0
h-index: 0
机构:
Merck Sharp Dohme Res Labs, Hoddesdon EN11 9BU, Herts, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Skidmore, John
论文数: 0 引用数: 0
h-index: 0
机构:
GlaxoSmithKline, Neurosci Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England

Dixon, Darren J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England Univ Oxford, Chem Res Lab, Dept Chem, Oxford OX1 3TA, England