共 115 条
Chiral CpxRhodium(III)-Catalyzed Enantioselective Aziridination of Unactivated Terminal Alkenes
被引:16
作者:

Wang, Juanjuan
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Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China

Luo, Mu-Peng
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Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China

Gu, Yi-Jie
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Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China

Liu, Yu-Ying
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Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China

Yin, Qin
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机构:
Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China

Wang, Shou-Guo
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Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
机构:
[1] Chinese Acad Sci, Shenzhen Inst Adv Technol, Shenzhen 518055, Guangdong, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金:
中国国家自然科学基金;
关键词:
Chiral Rhodium Catalysis;
Chiral Aziridines;
Enantioselective Aziridination;
Unactivated Alkenes;
C-H FUNCTIONALIZATION;
NITROGEN-ATOM TRANSFER;
ASYMMETRIC TRANSFER;
TRANSFER-HYDROGENATION;
CYCLOPENTADIENYL;
COMPLEXES;
LIGANDS;
ALCOHOLS;
ACTIVATION;
ANTIBIOTICS;
D O I:
10.1002/anie.202400502
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
Chiral cyclopentadienyl-rhodium(III) CpxRh(III) catalysis has been demonstrated to be competent for catalyzing highly enantioselective aziridination of challenging unactivated terminal alkenes and nitrene sources. The chiral CpxRh(III) catalysis system exhibited outstanding catalytic performance and wide functional group tolerance, yielding synthetically important and highly valuable chiral aziridines with good to excellent yields and enantioselectivities (up to 99 % yield, 93 % ee). This protocol presents a novel and effective strategy for synthesizing enantioenriched aziridines from simple alkenes. Various transformations were performed on the aziridine products, illustrating the versatility and synthetic potential of this protocol for constructing highly functionalized compounds.
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[1]
Transition Metal Catalyzed Enantioselective C(sp2)-H Bond Functionalization
[J].
Achar, Tapas Kumar
;
Maiti, Sudip
;
Jana, Sadhan
;
Maiti, Debabrata
.
ACS CATALYSIS,
2020, 10 (23)
:13748-13793

Achar, Tapas Kumar
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

Maiti, Sudip
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

Jana, Sadhan
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India

Maiti, Debabrata
论文数: 0 引用数: 0
h-index: 0
机构:
Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India Indian Inst Technol, Dept Chem, Mumbai 400076, Maharashtra, India
[2]
The conversion of allenes to strained three-membered heterocycles
[J].
Adams, C. S.
;
Weatherly, C. D.
;
Burke, E. G.
;
Schomaker, J. M.
.
CHEMICAL SOCIETY REVIEWS,
2014, 43 (09)
:3136-3163

Adams, C. S.
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

Weatherly, C. D.
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

Burke, E. G.
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

Schomaker, J. M.
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
[3]
Tunable, Chemo- and Site-Selective Nitrene Transfer Reactions through the Rational Design of Silver(I) Catalysts
[J].
Alderson, Juliet M.
;
Corbin, Joshua R.
;
Schomaker, Jennifer M.
.
ACCOUNTS OF CHEMICAL RESEARCH,
2017, 50 (09)
:2147-2158

Alderson, Juliet M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

Corbin, Joshua R.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

Schomaker, Jennifer M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA
[4]
Instantaneous Deprotection of Tosylamides and Esters with SmI2/Amine/Water
[J].
Ankner, Tobias
;
Hilmersson, Goeran
.
ORGANIC LETTERS,
2009, 11 (03)
:503-506

Ankner, Tobias
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden

Hilmersson, Goeran
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden Univ Gothenburg, Dept Chem, SE-41296 Gothenburg, Sweden
[5]
ANTIBIOTICS PRODUCED BY STREPTOMYCES-FICELLUS .1. FICELLOMYCIN
[J].
ARGOUDELIS, AD
;
REUSSER, F
;
WHALEY, HA
;
BACZYNSKYJ, L
;
MIZSAK, SA
;
WNUK, RJ
.
JOURNAL OF ANTIBIOTICS,
1976, 29 (10)
:1001-1006

ARGOUDELIS, AD
论文数: 0 引用数: 0
h-index: 0
机构:
UPJOHN CO,RES LABS,KALAMAZOO,MI 49001 UPJOHN CO,RES LABS,KALAMAZOO,MI 49001

REUSSER, F
论文数: 0 引用数: 0
h-index: 0
机构:
UPJOHN CO,RES LABS,KALAMAZOO,MI 49001 UPJOHN CO,RES LABS,KALAMAZOO,MI 49001

WHALEY, HA
论文数: 0 引用数: 0
h-index: 0
机构:
UPJOHN CO,RES LABS,KALAMAZOO,MI 49001 UPJOHN CO,RES LABS,KALAMAZOO,MI 49001

BACZYNSKYJ, L
论文数: 0 引用数: 0
h-index: 0
机构:
UPJOHN CO,RES LABS,KALAMAZOO,MI 49001 UPJOHN CO,RES LABS,KALAMAZOO,MI 49001

MIZSAK, SA
论文数: 0 引用数: 0
h-index: 0
机构:
UPJOHN CO,RES LABS,KALAMAZOO,MI 49001 UPJOHN CO,RES LABS,KALAMAZOO,MI 49001

WNUK, RJ
论文数: 0 引用数: 0
h-index: 0
机构:
UPJOHN CO,RES LABS,KALAMAZOO,MI 49001 UPJOHN CO,RES LABS,KALAMAZOO,MI 49001
[6]
Mild complexation protocol for chiral CpxRh and Ir complexes suitable for in situ catalysis
[J].
Audic, B.
;
Wodrich, M. D.
;
Cramer, N.
.
CHEMICAL SCIENCE,
2019, 10 (03)
:781-787

Audic, B.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, BCH 4305, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, BCH 4305, CH-1015 Lausanne, Switzerland

Wodrich, M. D.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCMD, Lab Computat Mol Design, BCH 5312, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, BCH 4305, CH-1015 Lausanne, Switzerland

Cramer, N.
论文数: 0 引用数: 0
h-index: 0
机构:
EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, BCH 4305, CH-1015 Lausanne, Switzerland EPFL SB ISIC LCSA, Lab Asymmetr Catalysis & Synth, BCH 4305, CH-1015 Lausanne, Switzerland
[7]
Mitomycinoid Alkaloids: Mechanism of Action, Biosynthesis, Total Syntheses, and Synthetic Approaches
[J].
Bass, Phillip D.
;
Gubler, Daniel A.
;
Judd, Ted C.
;
Williams, Robert M.
.
CHEMICAL REVIEWS,
2013, 113 (08)
:6816-6863

Bass, Phillip D.
论文数: 0 引用数: 0
h-index: 0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

Gubler, Daniel A.
论文数: 0 引用数: 0
h-index: 0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

Judd, Ted C.
论文数: 0 引用数: 0
h-index: 0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

Williams, Robert M.
论文数: 0 引用数: 0
h-index: 0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Univ Colorado Canc Ctr, Aurora, CO 80045 USA Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
[8]
A Synthesis of Pseudoconhydrine and Its Epimer via Hydroformylation and Dihydroxylation
[J].
Bates, Roderick W.
;
Sivarajan, K.
;
Straub, Bernd F.
.
JOURNAL OF ORGANIC CHEMISTRY,
2011, 76 (16)
:6844-6848

Bates, Roderick W.
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

Sivarajan, K.
论文数: 0 引用数: 0
h-index: 0
机构:
Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

Straub, Bernd F.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
[9]
Stereodivergent Catalysis
[J].
Beletskaya, Irina P.
;
Najera, Carmen
;
Yus, Miguel
.
CHEMICAL REVIEWS,
2018, 118 (10)
:5080-5200

Beletskaya, Irina P.
论文数: 0 引用数: 0
h-index: 0
机构:
Moscow MV Lomonosov State Univ, Chem Dept, Leninskie Gory 1, Moscow 117911, Russia Moscow MV Lomonosov State Univ, Chem Dept, Leninskie Gory 1, Moscow 117911, Russia

论文数: 引用数:
h-index:
机构:

Yus, Miguel
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Alicante, Dept Quim Organ, Apdo 99, E-03080 Alicante, Spain
Univ Alicante, Ctr Innovac Quim Avanzada ORFEO, CINQA, Apdo 99, E-03080 Alicante, Spain Moscow MV Lomonosov State Univ, Chem Dept, Leninskie Gory 1, Moscow 117911, Russia
[10]
Rhodium(II)-Catalyzed Enantioselective Intermolecular Aziridination of Alkenes
[J].
Boquet, Vincent
;
Nasrallah, Ali
;
Dana, Alejandro L.
;
Brunard, Erwan
;
Di Chenna, Pablo H.
;
Duran, Fernando J.
;
Retailleau, Pascal
;
Darses, Benjamin
;
Sircoglou, Marie
;
Dauban, Philippe
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2022, 144 (37)
:17156-17164

Boquet, Vincent
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Nasrallah, Ali
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Dana, Alejandro L.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Buenos Aires, CONICET, UMYMFOR, C1428EGA, Buenos Aires, Argentina
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, C1428EGA, Buenos Aires, Argentina Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Brunard, Erwan
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Di Chenna, Pablo H.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Buenos Aires, CONICET, UMYMFOR, C1428EGA, Buenos Aires, Argentina
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, C1428EGA, Buenos Aires, Argentina Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Duran, Fernando J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Buenos Aires, CONICET, UMYMFOR, C1428EGA, Buenos Aires, Argentina
Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, C1428EGA, Buenos Aires, Argentina Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Retailleau, Pascal
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Darses, Benjamin
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Grenoble Alpes, CNRS, DCM, F-38000 Grenoble, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Sircoglou, Marie
论文数: 0 引用数: 0
h-index: 0
机构:
CNRS, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France

Dauban, Philippe
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France Univ Paris Saclay, Inst Chim Subst Nat, CNRS, UPR 2301, F-91198 Gif Sur Yvette, France