Enantioconvergent Negishi Cross-Couplings of Racemic Secondary Organozinc Reagents to Access Privileged Scaffolds: A Combined Experimental and Theoretical Study

被引：0

作者：

Preinfalk, Alexander ^{[1
]}

Oost, Rik ^{[1
]}

Menger, Maximilian F. S. J. ^{[2
]}

Simaan, Marwan ^{[1
]}

Lemouzy, Sebastien ^{[1
]}

Senoner, Samuel ^{[1
]}

Shaaban, Saad ^{[1
]}

Maryasin, Boris ^{[1
,2
]}

Gonzalez, Leticia ^{[2
]}

Maulide, Nuno ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, Wahringer Str 38, A-1090 Vienna, Austria

[2] Univ Vienna, Inst Theoret Chem, Wahringer Str 17, A-1090 Vienna, Austria

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2024年 / 63卷 / 50期

关键词：

Organozinc; Palladium; TADDOL; phosphite; DFT; Asymmetric catalysis; QUANTUM-CHEMISTRY; ESTERS;

D O I：

10.1002/anie.202414868

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioconvergent palladium-catalyzed Negishi cross-coupling with racemic secondary organozinc reagents has been developed, enabling access to enantioenriched 1,1-diarylalkane motifs in high yields and enantioselectivities. Computational data indicates that the racemization of organozinc compounds most likely occurs through a bridged bimolecular mechanism.

引用

页数：7

共 7 条

[1] Enantioconvergent cross-coupling of racemic secondary organozinc reagents
Oost, Rik
Preinfalk, Alexander
Misale, Antonio
Maulide, Nuno
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
[2] Asymmetric nickel-catalyzed negishi cross-couplings of secondary α-bromo amides with organozinc reagents
Fischer, C
Fu, GC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4594 - 4595
[3] Enantioconvergent Cross-Couplings of Racemic Alkylmetal Reagents with Unactivated Secondary Alkyl Electrophiles: Catalytic Asymmetric Negishi α-Alkylations of N-Boc-pyrrolidine
Cordier, Christopher J.
Lundgren, Rylan J.
Fu, Gregory C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (30) : 10946 - 10949
[4] Negishi cross-couplings of unsaturated halides bearing relatively acidic hydrogen atoms with organozinc reagents
Manolikakes, Georg
Schade, Matthias A.
Hernandez, Carmen Munoz
Mayr, Herbert
Knochel, Paul
ORGANIC LETTERS, 2008, 10 (13) : 2765 - 2768
[5] Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents
Binder, Jorg T.
Cordier, Christopher J.
Fu, Gregory C.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (41) : 17003 - 17006
[6] NICKEL-CATALYZED ENANTIOSELECTIVE NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY alpha-BROMO AMIDES WITH ALKYLZINC REAGENTS: (S)-N-BENZYL-7-CYANO-2-ETHYL-N-PHENYLHEPTANAMIDE
Lou, Sha
Fu, Gregory C.
ORGANIC SYNTHESES, 2010, 87 : 330 - +
[7] NICKEL-CATALYZED ASYMMETRIC NEGISHI CROSS-COUPLINGS OF RACEMIC SECONDARY ALLYLIC CHLORIDES WITH ALKYLZINCS: (S,E)-ETHYL 6-(1,3-DIOXOLAN-2-YL)-4-METHYLHEX-2-ENOATE
Lou, Sha
Fu, Gregory C.
ORGANIC SYNTHESES, 2010, 87 : 317 - +

← 1 →