An Asymmetric Transformation of Symmetrical Epoxides to Both Enantiomers of Allylic Alcohols by Chiral Lithium Amides

1987 ◽  
Vol 16 (2) ◽  
pp. 389-392 ◽  
Author(s):  
Masatoshi Asami ◽  
Hiroto Kirihara
Keyword(s):  
Allylic Alcohols ◽  
Lithium Amides ◽  
Asymmetric Transformation

scholarly journals Palladium-Catalyzed Functionalization of Olefins and Alkynes: From Oxyalkynylation to Tethered Dynamic Kinetic Asymmetric Transformations (DYKAT)

Synlett ◽  
2020 ◽  
Author(s):  
Stefano Nicolai ◽  
Ugo Orcel ◽  
Bastian Muriel ◽  
Phillip D. G. Greenwood ◽  
Luca Buzzetti ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Amino Alcohols ◽  
Chiral Auxiliary ◽  
Allylic Alcohols ◽  
Personal Account ◽  
Allylic Amines ◽  
Asymmetric Transformations ◽  
Palladium Catalyzed ◽  
Asymmetric Transformation

AbstractThis review presents an account of the palladium-catalyzed functionalizations of alkenes and alkynes developed at the Laboratory of Catalysis and Organic Synthesis (LCSO). Starting from the intramolecular oxy- and aminoalkynylation of alkenes, tethered methods were then developed to functionalize allylic amines and alcohols, as well as propargylic amines. Finally, a new dynamic kinetic asymmetric transformation was developed based on the use of a ‘one-arm’ Trost-type ligand, giving access to enantiopure amino alcohols. Each section is a personal account by the researcher(s) who performed the work.1 Introduction,2 Oxy- and Aminoalkynylation of Olefins,3 In Situ Tethering Strategies for the Synthesis of Vicinal Amino Alcohols and Diamines,4 Carboamination of Allylic Alcohols,5 Carbooxygenation of Propargylic Amines,6 Enantioselective Carboetherification/Hydrogenation via a Catalytically Formed Chiral Auxiliary,7 Conclusion

Active MnO2 As a Mild Oxidizing Reagent for the Controlled Oxidation of Benzylic and Allylic Alcohols

2012 ◽  
Vol 2 (6) ◽  
pp. 48-48
Author(s):  
Y. M. Nandurkar Y. M. Nandurkar ◽  
◽  
B. B. Bahule B. B. Bahule
Keyword(s):  
Allylic Alcohols

Bimetallic Radical Redox-Relay Catalysis for the Isomerization of Epoxides to Allylic Alcohols

2019 ◽  
Author(s):  
Ke-Yin Ye ◽  
Terry McCallum ◽  
Song Lin
Keyword(s):  
Ring Opening ◽  
High Reactivity ◽  
Hydrogen Atom Transfer ◽  
Organic Radicals ◽  
Epoxide Ring ◽  
Allylic Alcohols ◽  
Epoxide Ring Opening ◽  
Bond Forming ◽  
Co Catalysts ◽  
The Rich

Organic radicals are generally short-lived intermediates with exceptionally high reactivity. Strategically, achieving synthetically useful transformations mediated by organic radicals requires both efficient initiation and selective termination events. Here, we report a new catalytic strategy, namely bimetallic radical redox-relay, in the regio- and stereoselective rearrangement of epoxides to allylic alcohols. This approach exploits the rich redox chemistry of Ti and Co complexes and merges reductive epoxide ring opening (initiation) with hydrogen atom transfer (termination). Critically, upon effecting key bond-forming and -breaking events, Ti and Co catalysts undergo proton-transfer/electron-transfer with one another to achieve turnover, thus constituting a truly synergistic dual catalytic system.<br>

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