Toward the Development of a General Chiral Auxiliary. A Remarkable, Highly Diastereoselective, Auxiliary-Mediated Substitution:  Application to an Enantioselective Synthesis of the Cyclohexene Subunit of (+)-Tetronolide

1996 ◽  
Vol 61 (21) ◽  
pp. 7238-7239 ◽  
Author(s):  
Robert K. Boeckman, ◽  
Stephen T. Wrobleski
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliary

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

Enantioselective Synthesis of β-Lactams Using a Chiral Auxiliary

Synlett ◽  
2006 ◽  
Vol 2006 (07) ◽  
pp. 1113-1115 ◽  
Author(s):  
Yan-Guang Wang ◽  
Qing Yuan ◽  
Shan-Zhong Jian
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliary

Enantioselective Synthesis ofα-Hydroxy Acids Employing (1S)-(+)-N,N-Diisopropyl-10-camphorsulfonamide as Chiral Auxiliary

1999 ◽  
Vol 1 (13) ◽  
pp. 2061-2063 ◽  
Author(s):  
Jia-Wen Chang ◽  
Der-Pin Jang ◽  
Biing-Jiun Uang ◽  
Fen-Ling Liao ◽  
Sue-Lein Wang
Keyword(s):  
Enantioselective Synthesis ◽  
Chiral Auxiliary ◽  
Hydroxy Acids
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