ChemInform Abstract: Asymmetric Induction in Intramolecular SN2′ Reaction. Enantioselective Synthesis of Cyclopenta[b]benzofuran with Chiral Lithium Alkoxides.

ChemInform ◽  
2010 ◽  
Vol 29 (4) ◽  
pp. no-no
Author(s):  
H. NISHIYAMA ◽  
N. SAKATA ◽  
Y. MOTOYAMA ◽  
H. WAKITA ◽  
H. NAGASE
Keyword(s):  
Enantioselective Synthesis ◽  
Asymmetric Induction ◽  
Sn2 Reaction

Asymmetric Induction in Intramolecular SN2' Reaction. Enantioselective Synthesis of Cyclopenta[b]benzofuran with Chiral Lithium Alkoxides

Synlett ◽  
1997 ◽  
Vol 1997 (10) ◽  
pp. 1147-1148 ◽  
Author(s):  
Hisao Nishiyama ◽  
Naoya Sakata ◽  
Yukihiro Motoyama ◽  
Hisanori Wakita ◽  
Hiroshi Nagase
Keyword(s):  
Enantioselective Synthesis ◽  
Asymmetric Induction ◽  
Sn2 Reaction

ChemInform Abstract: 1,3-Asymmetric Induction via 1,5-Hydrogen Atom Translocation Reactions. Highly Enantioselective Synthesis of β-Substituted β-Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 28 (1) ◽  
pp. no-no
Author(s):  
F. BEAULIEU ◽  
J. ARORA ◽  
U. VEITH ◽  
N. J. TAYLOR ◽  
B. J. CHAPELL ◽  
...  
Keyword(s):  
Amino Acids ◽  
Hydrogen Atom ◽  
Enantioselective Synthesis ◽  
Asymmetric Induction

scholarly journals Organocatalytic Discrimination of Non-Directing Aryl and Heteroaryl Groups: Enantioselective Synthesis of Bioactive Indole-Containing Triarylmethanes

2021 ◽  
Author(s):  
Qiaolin Yan ◽  
Meng Duan ◽  
Cien Chen ◽  
Zhiqin Deng ◽  
Mandi Wu ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Spatial Interaction ◽  
Antiviral Drug ◽  
Kinetic Studies ◽  
Enantioselective Synthesis ◽  
Asymmetric Induction ◽  
Efficient Access ◽  
Chiral Phosphoric Acid ◽  
Biological Studies ◽  
Directing Group

Despite the enormous developments of asymmetric catalysis, the basis for asymmetric induction is largely limited to spatial interaction between substrate and catalyst. Consequently, asymmetric discrimination between two sterically similar groups remains a challenge. This is particularly formidable for enantiodifferentiation between aryl and heteroaryl groups without a directing group or electronic manipulation. Here we address this challenge by a robust organocatalytic system leading to excellent enantioselection between aryl and heteroaryl groups. With the versatile 2-indole imine methide as platform, an excellent combination of a superb chiral phosphoric acid and the optimal hydride source provided efficient access to a range of highly enantioenriched indole-containing triarylmethanes. Control experiments and kinetic studies provided important insights into the mechanism. DFT calculations also indicated that, while hydrogen bonding is important for activation, the key interaction for discrimination of the two aryl groups is mainly π-π stacking. Preliminary biological studies also demonstrated the great potential of these triarylmethanes for anticancer and antiviral drug development.

Enantioselective synthesis of mosquito oviposition pheromone and its epimer from a naturally occurring fatty acid

RSC Advances ◽  
2015 ◽  
Vol 5 (123) ◽  
pp. 101732-101739 ◽  
Author(s):  
David Hurem ◽  
Travis Dudding
Keyword(s):  
Fatty Acid ◽  
Late Stage ◽  
Enantioselective Synthesis ◽  
Asymmetric Induction ◽  
Hexadecenoic Acid ◽  
Naturally Occurring ◽  
Mosquito Oviposition ◽  
Asymmetric Transformation

Direct epoxidation of cis-5-hexadecenoic acid towards the synthesis of Mosquito Oviposition Pheromone (MOP) and evaluation of Dynamic Kinetic Asymmetric Transformation (DYKAT) for late-stage asymmetric induction are presented.

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