Transition metal catalyzed nucleophilic allylic substitution: activation of allylic alcohols via π-allylic species

2012 ◽  
Vol 41 (12) ◽  
pp. 4467 ◽  
Author(s):  
Basker Sundararaju ◽  
Mathieu Achard ◽  
Christian Bruneau
Keyword(s):  
Transition Metal ◽  
Allylic Alcohols ◽  
Allylic Substitution ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Transition-Metal-Catalyzed Allylic Substitution and Titanocene-Catalyzed Epoxypolyene Cyclization as a Powerful Tool for the Preparation of Terpenoids.

ChemInform ◽  
2006 ◽  
Vol 37 (52) ◽  
Author(s):  
Andreas Gansaeuer ◽  
Jose Justicia ◽  
Antonio Rosales ◽  
Dennis Worgull ◽  
Bjoern Rinker ◽  
...  
Keyword(s):  
Transition Metal ◽  
Allylic Substitution ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates

2015 ◽  
Vol 44 (22) ◽  
pp. 7929-7967 ◽  
Author(s):  
Nicholas A. Butt ◽  
Wanbin Zhang
Keyword(s):  
Transition Metal ◽  
Allylic Substitution ◽  
Substitution Reactions ◽  
Recent Developments ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

This review highlights recent developments in the area of transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates.

Hydroxylamines as Oxygen Atom Nucleophiles in Transition-Metal-Catalyzed Allylic Substitution

2005 ◽  
Vol 70 (6) ◽  
pp. 2148-2153 ◽  
Author(s):  
Hideto Miyabe ◽  
Kazumasa Yoshida ◽  
Masashige Yamauchi ◽  
Yoshiji Takemoto
Keyword(s):  
Transition Metal ◽  
Oxygen Atom ◽  
Allylic Substitution ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

Iridium-catalyzed Z-retentive asymmetric allylic substitution reactions

Science ◽  
2021 ◽  
Vol 371 (6527) ◽  
pp. 380-386 ◽  
Author(s):  
Ru Jiang ◽  
Lu Ding ◽  
Chao Zheng ◽  
Shu-Li You
Keyword(s):  
Transition Metal ◽  
Optically Active ◽  
Promising Method ◽  
Allylic Substitution ◽  
Substitution Reactions ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Quaternary Stereocenter ◽  
Thermodynamic Instability

Z-Olefins are challenging synthetic targets owing to their relative thermodynamic instability. Transition metal–catalyzed asymmetric allylic substitution reactions are well known for installing stereocenters adjacent to branched or E-linear olefins. However, analogous reactions for the synthesis of optically active Z-olefin products are rare. Here we report iridium-catalyzed asymmetric allylic substitution reactions that retain Z-olefin geometries while establishing an adjacent quaternary stereocenter. The formation of transient anti-π-allyl-iridium intermediates and their capture by external nucleophiles before isomerization to the thermodynamically more stable syn-π-allyl-iridium counterparts have been observed. These results provide a promising method for preparing chiral Z-olefinic compounds.

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