Pseudomonas oleovorans monooxygenase-catalyzed asymmetric epoxidation of allyl alcohol derivatives and hydroxylation of a hypersensitive radical probe with the radical ring-opening rate exceeding the oxygen-rebound rate

1991 ◽  
Vol 113 (15) ◽  
pp. 5878-5880 ◽  
Author(s):  
Hong Fu ◽  
Martin Newcomb ◽  
Chi Huey Wong
Keyword(s):  
Allyl Alcohol ◽  
Ring Opening ◽  
Asymmetric Epoxidation ◽  
Pseudomonas Oleovorans ◽  
Radical Ring

scholarly journals Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

2016 ◽  
Vol 12 ◽  
pp. 1765-1771 ◽  
Author(s):  
Pramod R Markad ◽  
Navanath Kumbhar ◽  
Dilip D Dhavale
Keyword(s):  
Amino Acid ◽  
Allyl Alcohol ◽  
Ring Opening ◽  
Functional Group ◽  
Asymmetric Epoxidation ◽  
Oxirane Ring ◽  
Trimethyl Borate ◽  
Pyranose Ring ◽  
Acid Catalyzed ◽  
Sharpless Asymmetric Epoxidation

The C8’-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to the formation of the pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 12. Functional group manipulation in 12 gave 21 that on stereoselective β-glycosylation afforded the pyranosyl thymine nucleoside 2 – a core of amipurimycin.

TiCp2Cl-Catalyzed Living Radical and Ring Opening Polymerizations Initiated from Epoxides and Aldehydes in the Synthesis of Linear, Graft and Branched Polymers

2004 ◽  
Vol 856 ◽  
Author(s):  
Alexandru D. Asandei ◽  
Isaac W. Moran ◽  
Gobinda Saha ◽  
Yanhui Chen
Keyword(s):  
Electron Transfer ◽  
Ring Opening ◽  
Glycidyl Methacrylate ◽  
Ring Opening Polymerization ◽  
Branched Polymers ◽  
Single Electron Transfer ◽  
Radical Ring ◽  
Polymer Architectures ◽  
Complex Polymer

ABSTRACTTi(III)Cp2Cl-catalyzed radical ring opening (RRO) of epoxides or single electron transfer (SET) reduction of aldehydes generates Ti alkoxides and carbon centered radicals which add to styrene, initiating a radical polymerization. This polymerization is mediate in a living fashion by the reversible termination of growing chains with the TiCp2Cl metalloradical. In addition, polymers or monomers containing pendant epoxide groups (glycidyl methacrylate) can be used as substrates for radical grafting or branching reactions by self condensing vinyl polymerization. In addition, Ti alkoxides generated in situ by both epoxide RRO and aldehyde SET initiate the living ring opening polymerization of ε-caprolactone. Thus, new initiators and catalysts are introduced for the synthesis of complex polymer architectures.

Radical Ring-Opening Copolymerization of 2-Methylene 1,3-Dioxepane and Methyl Methacrylate:  Experiments Originally Designed To Probe the Origin of the Penultimate Unit Effect

1999 ◽  
Vol 32 (5) ◽  
pp. 1332-1340 ◽  
Author(s):  
G. Evan Roberts ◽  
Michelle L. Coote ◽  
Johan P. A. Heuts ◽  
Leesa M. Morris ◽  
Thomas P. Davis
Keyword(s):  
Methyl Methacrylate ◽  
Ring Opening ◽  
Radical Ring

Scope and limitations of the nitroxide-mediated radical ring-opening polymerization of cyclic ketene acetals

2013 ◽  
Vol 4 (17) ◽  
pp. 4776 ◽  
Author(s):  
Antoine Tardy ◽  
Vianney Delplace ◽  
Didier Siri ◽  
Catherine Lefay ◽  
Simon Harrisson ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Polymerization ◽  
Radical Ring ◽  
Cyclic Ketene Acetals ◽  
Ketene Acetals
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