Methylation and hydroxymethylation of allylic alcohols via radical cyclization. Methodology for stereoselective construction of an aliphatic chain in application to sterol synthesis

1990 ◽  
Vol 55 (11) ◽  
pp. 3484-3492 ◽  
Author(s):  
Alicja Kurek-Tyrlik ◽  
Jerzy Wicha ◽  
Andrzej Zarecki ◽  
Guenther Snatzke
Keyword(s):  
Radical Cyclization ◽  
Sterol Synthesis ◽  
Allylic Alcohols ◽  
Aliphatic Chain

Silylmethyl radical cyclization: new stereoselective method for 1,3-diol synthesis from allylic alcohols

1984 ◽  
Vol 49 (12) ◽  
pp. 2298-2300 ◽  
Author(s):  
Hisao Nishiyama ◽  
Toshio Kitajima ◽  
Makoto Matsumoto ◽  
Kenji Itoh
Keyword(s):  
Radical Cyclization ◽  
Allylic Alcohols ◽  
Stereoselective Method

Tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds

2017 ◽  
Vol 15 (15) ◽  
pp. 3239-3247 ◽  
Author(s):  
Zhen Zhang ◽  
Cheng Li ◽  
Shao-Hua Wang ◽  
Fu-Min Zhang ◽  
Xue Han ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Radical Cyclization ◽  
Allylic Alcohols ◽  
Dicarbonyl Compounds ◽  
Oxidative Radical Cyclization

Herein we present a novel tandem SN2′ nucleophilic substitution/oxidative radical cyclization of aryl substituted allylic alcohols with 1,3-dicarbonyl compounds.

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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