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>

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>

Novel Chiral Ligands for Palladium-catalyzed Asymmetric Allylic Alkylation/ Asymmetric Tsuji-Trost Reaction: A Review

2019 ◽  
Vol 23 (11) ◽  
pp. 1168-1213 ◽  
Author(s):  
Samar Noreen ◽  
Ameer Fawad Zahoor ◽  
Sajjad Ahmad ◽  
Irum Shahzadi ◽  
Ali Irfan ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Enantioselective Synthesis ◽  
Chiral Ligands ◽  
Allylic Alkylation ◽  
Research Groups ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Potential ◽  
Long Time ◽  
Palladium Catalyzed ◽  
Alkylation Reactions

Background: Asymmetric catalysis holds a prestigious role in organic syntheses since a long time and chiral inductors such as ligands have been used to achieve the utmost desired results at this pitch. The asymmetric version of Tsuji-Trost allylation has played a crucial role in enantioselective synthesis. Various chiral ligands have been known for Pdcatalyzed Asymmetric Allylic Alkylation (AAA) reactions and exhibited excellent catalytic potential. The use of chiral ligands as asymmetric inductors has widened the scope of Tsuji-Trost allylic alkylation reactions. Conclusion: Therefore, in this review article, a variety of chiral inductors or ligands have been focused for palladium catalyzed asymmetric allylic alkylation (Tsuji-Trost allylation) and in this regard, recently reported literature (2013-2017) has been described. The use of ligands causes the induction of enantiodiscrimination to the allylated products, therefore, the syntheses of various kinds of ligands have been targeted by many research groups to employ in Pd-catalyzed AAA reactions.

ChemInform Abstract: “Evans Auxiliary” Based P-N Ligands for Pd-Catalyzed Asymmetric Allylic Alkylation Reactions.

ChemInform ◽  
2012 ◽  
Vol 43 (46) ◽  
pp. no-no
Author(s):  
Yun Li ◽  
Fang Liang ◽  
Rui Wu ◽  
Qian Li ◽  
Quan-Rui Wang ◽  
...  
Keyword(s):  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Alkylation Reactions

Synthesis of highly rigid phosphine–oxazoline ligands for palladium-catalyzed asymmetric allylic alkylation

2018 ◽  
Vol 16 (41) ◽  
pp. 7717-7724 ◽  
Author(s):  
Zhongxuan Qiu ◽  
Rui Sun ◽  
Dawei Teng
Keyword(s):  
Catalytic Performance ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Palladium Catalyzed ◽  
Alkylation Reactions ◽  
Stereogenic Center ◽  
Oxazoline Ligands ◽  
Excellent Catalytic Performance

Rigid phosphine–oxazoline ligands with a spirocarbon stereogenic center were developed, which exhibited excellent catalytic performance for Pd-catalyzed allylic alkylation reactions.

Novel chiral P,O-ligands for homogeneous Pd(0) catalysed asymmetric allylic alkylation reactions

2008 ◽  
Vol 19 (4) ◽  
pp. 454-458 ◽  
Author(s):  
Vanda Raquel Marinho ◽  
Ana Isabel Rodrigues ◽  
Anthony J. Burke
Keyword(s):  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Alkylation Reactions
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