Approach to Phenanthroindolizidine Alkaloids Using Organic Azides with 1-Aryl Allylic Alcohols: Unexpected Tandem Reactions to Indenyl Aziridines via Nazarov Cyclization

Heterocycles ◽  
2016 ◽  
Vol 92 (7) ◽  
pp. 1313 ◽  
Author(s):  
Hiroki Tanimoto ◽  
Taiki Yokoi ◽  
Takahiro Sugiura ◽  
Tsumoru Morimoto ◽  
Yasuhiro Nishiyama ◽  
...  
Keyword(s):  
Allylic Alcohols ◽  
Tandem Reactions ◽  
Nazarov Cyclization ◽  
Organic Azides ◽  
Phenanthroindolizidine Alkaloids

scholarly journals Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles

2011 ◽  
Vol 7 ◽  
pp. 786-793 ◽  
Author(s):  
Estela Álvarez ◽  
Delia Miguel ◽  
Patricia García-García ◽  
Manuel A Fernández-Rodríguez ◽  
Félix Rodríguez ◽  
...  
Keyword(s):  
Proper Choice ◽  
Tandem Reaction ◽  
Tandem Reactions ◽  
Nazarov Cyclization ◽  
Reaction Conditions

The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl)indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles.

Tandem Reactions with Chiral Enolates: Preparation of Allylic Alcohols via Trapping with Vinyl Oxiranes

2010 ◽  
Vol 12 (3) ◽  
pp. 576-579 ◽  
Author(s):  
Matthias Welker ◽  
Simon Woodward ◽  
Alexandre Alexakis
Keyword(s):  
Allylic Alcohols ◽  
Tandem Reactions ◽  
Chiral Enolates

Enabling Selective Tandem Reactions via Catalyst Architecture Engineering

2020 ◽  
Vol 2 (10) ◽  
pp. 929-941
Author(s):  
Hong Je Cho ◽  
Bingjun Xu
Keyword(s):  
Tandem Reactions

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>

Enantioselective Synthesis of Chromanones through Organocatalytic Tandem Reactions

2020 ◽  
Vol 362 (23) ◽  
pp. 5524-5528
Author(s):  
Mengxue Lu ◽  
Xin Wang ◽  
Zongli Xiong ◽  
Jingxiang Duan ◽  
Wen Ren ◽  
...  
Keyword(s):  
Enantioselective Synthesis ◽  
Tandem Reactions
Sign in / Sign up

Export Citation Format

Share Document