scholarly journals Copper-Catalyzed Asymmetric Allylic Alkylation ofβ-Keto Esters with Allylic Alcohols

2017 ◽  
Vol 359 (10) ◽  
pp. 1735-1741 ◽  
Author(s):  
Paz Trillo ◽  
Alejandro Baeza
Keyword(s):  
Allylic Alcohols ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Keto Esters

scholarly journals Asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates with α-fluoro-β-keto esters

2013 ◽  
Vol 9 ◽  
pp. 1853-1857 ◽  
Author(s):  
Lin Yan ◽  
Zhiqiang Han ◽  
Bo Zhu ◽  
Caiyun Yang ◽  
Choon-Hong Tan ◽  
...  
Keyword(s):  
Fluorine Atom ◽  
Allylic Alkylation ◽  
Quaternary Carbon ◽  
Asymmetric Allylic Alkylation ◽  
Keto Esters

In the presence of a commercially available Cinchona alkaloid as catalyst, the asymmetric allylic alkylation of Morita–Baylis–Hillman carbonates, with α-fluoro-β-keto esters as nucleophiles, have been successfully developed. A series of important fluorinated adducts, with chiral quaternary carbon centres containing a fluorine atom, was achieved in good yields (up to 93%), with good to excellent enantioselectivities (up to 96% ee) and moderate diastereoselectivities (up to 4:1 dr).

scholarly journals Iridium-Catalyzed Asymmetric α-Allylic Alkylation of Amides using Vinyl Azide as Amide Enolate Surrogate

2020 ◽  
Author(s):  
Aditya Chakrabarty ◽  
Santanu Mukherjee
Keyword(s):  
Electronic Properties ◽  
Reaction Pathways ◽  
Allylic Alcohols ◽  
Allylic Alkylation ◽  
Atom Economy ◽  
Asymmetric Allylic Alkylation ◽  
Vinyl Azides ◽  
Alkylation Reactions ◽  
First Time

Among the unstabilized enolates used as nucleophile in iridium-catalyzed asymmetric allylic alkylation reactions, amide enolates are least explored. Vinyl azides are now employed as amide enolate surrogate for the first time in Ir-catalyzed asymmetric allylic alkylation with branched allylic alcohols as the allylic electrophile. Competing reaction pathways are suppressed through systematic tuning of steric and electronic properties of vinyl azide to effect α-allylic alkylation of secondary acetamides with high atom-economy, exclusive branched selectivity and moderate to excellent enantioselectivity.<br>

Asymmetric Allylic Alkylation of β-Ketoesters with Allylic Alcohols by a Nickel/Diphosphine Catalyst

2015 ◽  
Vol 55 (3) ◽  
pp. 1098-1101 ◽  
Author(s):  
Yusuke Kita ◽  
Rahul D. Kavthe ◽  
Hiroaki Oda ◽  
Kazushi Mashima
Keyword(s):  
Allylic Alcohols ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation
Sign in / Sign up

Export Citation Format

Share Document