Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B

2017 ◽  
Vol 56 (23) ◽  
pp. 6609-6612 ◽  
Author(s):  
Minami Odagi ◽  
Kota Furukori ◽  
Kan Takayama ◽  
Keiichi Noguchi ◽  
Kazuo Nagasawa
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Kinetic Resolution ◽  
Oxidative Kinetic Resolution ◽  
Rishirilide B

Total Synthesis of Rishirilide B by Organocatalytic Oxidative Kinetic Resolution: Revision of Absolute Configuration of (+)-Rishirilide B

2017 ◽  
Vol 129 (23) ◽  
pp. 6709-6712 ◽  
Author(s):  
Minami Odagi ◽  
Kota Furukori ◽  
Kan Takayama ◽  
Keiichi Noguchi ◽  
Kazuo Nagasawa
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Kinetic Resolution ◽  
Oxidative Kinetic Resolution ◽  
Rishirilide B

Total synthesis of (R)-lipoic acid and (S)-lipoic acid via an Mn (III)-salen-catalyzed oxidative kinetic resolution

2015 ◽  
Vol 26 (5-6) ◽  
pp. 281-287 ◽  
Author(s):  
Abhijeet N. Purude ◽  
Kailash P. Pawar ◽  
Niteen B. Patil ◽  
Uttam R. Kalkote ◽  
Subhash P. Chavan
Keyword(s):  
Total Synthesis ◽  
Lipoic Acid ◽  
Kinetic Resolution ◽  
Oxidative Kinetic Resolution

Catalyst- and Silane- Controlled Enantioselective Hydrofunctionalization of Alkenes by Cobalt-Catalyzed Hydrogen Atom Transfer and Radical-Polar Crossover

2020 ◽  
Author(s):  
Kousuke Ebisawa ◽  
Kana Izumi ◽  
Yuka Ooka ◽  
Hiroaki Kato ◽  
Sayori Kanazawa ◽  
...  
Keyword(s):  
Hydrogen Atom ◽  
Absolute Configuration ◽  
Kinetic Resolution ◽  
Hydrogen Atom Transfer ◽  
Biologically Active ◽  
Atom Transfer ◽  
High Concentration ◽  
Chain Reaction ◽  
Radical Chain ◽  
Radical Chain Reaction

Catalytic enantioselective synthesis of tetrahydrofurans, which are found in the structures of many biologically active natural products, via a transition-metal catalyzed-hydrogen atom transfer (TM-HAT) and radical-polar crossover (RPC) mechanism is described herein. Hydroalkoxylation of non-conjugated alkenes proceeded efficiently with excellent enantioselectivity (up to 94% ee) using a suitable chiral cobalt catalyst, <i>N</i>-fluoro-2,4,6-collidinium tetrafluoroborate, and diethylsilane. Surprisingly, absolute configuration of the product was highly dependent on the steric hindrance of the silane. Slow addition of the silane, the dioxygen effect in the solvent, thermal dependency, and DFT calculation results supported the unprecedented scenario of two competing selective mechanisms. For the less-hindered diethylsilane, a high concentration of diffused carbon-centered radicals invoked diastereoenrichment of an alkylcobalt(III) intermediate by a radical chain reaction, which eventually determined the absolute configuration of the product. On the other hand, a more hindered silane resulted in less opportunity for radical chain reaction, instead facilitating enantioselective kinetic resolution during the late-stage nucleophilic displacement of the alkylcobalt(IV) intermediate.

Asymmetric Total Synthesis and Determination of the Absolute Configuration of (+)-Srilankenyne via Sequence-Sensitive Halogenations Guided by Conformational Analysis

2021 ◽  
Vol 23 (4) ◽  
pp. 1321-1326
Author(s):  
Hongjun Jang ◽  
Soo Yeon Kwak ◽  
Dongjoo Lee ◽  
Juan V. Alegre-Requena ◽  
Hyoungsu Kim ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Asymmetric Total Synthesis ◽  
The Absolute
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