Novel Applications of the Schoellkopf Chiral Auxiliary: A New and Efficient Enantioselective Synthesis of β-Lactams Possessing a C-4 Quaternary Stereocenter.

ChemInform ◽  
2004 ◽  
Vol 35 (14) ◽  
Author(s):  
Stamatia Vassiliou ◽  
Constantinos Dimitropoulos ◽  
Plato A. Magriotis
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliary ◽  
Quaternary Stereocenter ◽  
Novel Applications

Asymmetric Synthesis of α-Alkylated γ-Lactam via Nickel/8-Quinim-Catalyzed Reductive Alkyl-Carbamoylation of Unactivated Alkene

Synlett ◽  
2021 ◽  
Author(s):  
Xianqing Wu ◽  
Mohini Shrestha ◽  
Yifeng Chen
Keyword(s):  
Functional Group ◽  
Enantioselective Synthesis ◽  
Chiral Auxiliary ◽  
Alkyl Iodide ◽  
General Strategy ◽  
Chemical Bonds ◽  
Mild Conditions ◽  
Chiral Carbon ◽  
Enantioselective Reaction ◽  
Metal Catalyzed

AbstractChiral-auxiliary-mediated synthesis represents the most frequently used synthetic tool for the induction of chirality on α-position of γ-lactams in organic synthesis. However, the general strategy requires the stoichiometric use of chiral reagents with multiple manipulation steps. Transition-metal-catalyzed asymmetric alkene dicarbofunctionalization using readily available substrates under mild conditions allows the simultaneous construction of two vicinal chemical bonds and a chiral carbon center, hence, gain expedient access to chiral heterocycles. Herein, we disclose a Ni-catalyzed enantioselective reaction of 3-butenyl carbamoyl chloride and primary alkyl iodide enabled by a newly designed chiral 8-quinoline imidazoline ligand (8-Quinim). This protocol features broad functional group tolerance and high enantioselectivities, achieving unprecedented synthesis of chiral nonaromatic heterocycles via catalytic reductive protocol.1 Introduction2 Development of 8-Quinim Ligand3 Nickel/8-Quinim-Catalyzed Enantioselective Synthesis of Chiral α-Alkylated γ-Lactam4 Conclusion and Outlook

Palladium(ii)-catalyzed asymmetric C–H carbonylation to diverse isoquinoline derivatives bearing all-carbon quaternary stereocenters

2020 ◽  
Vol 56 (78) ◽  
pp. 11605-11608
Author(s):  
Yan Li ◽  
Xiu-Fen Cheng ◽  
Fan Fei ◽  
Tian-Rui Wu ◽  
Kang-Jie Bian ◽  
...  
Keyword(s):  
Late Stage ◽  
Enantioselective Synthesis ◽  
One Step ◽  
Quaternary Stereocenters ◽  
Quaternary Stereocenter ◽  
Isoquinoline Derivatives

Enantioselective synthesis of isoquinoline derivatives bearing an all-carbon quaternary stereocenter in one step via asymmetric Pd(ii)-catalyzed C–H activation and multiple late-stage derivatizations.

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