New 1,10-phenanthroline ligands for asymmetric catalysis: enantioselective palladium catalyzed allylic substitution

1998 ◽  
Vol 9 (15) ◽  
pp. 2575-2578 ◽  
Author(s):  
Giorgio Chelucci ◽  
Antonio Saba
Keyword(s):  
Asymmetric Catalysis ◽  
Allylic Substitution ◽  
Palladium Catalyzed ◽  
Phenanthroline Ligands

scholarly journals NeoPHOX – a structurally tunable ligand system for asymmetric catalysis

2016 ◽  
Vol 12 ◽  
pp. 1185-1195 ◽  
Author(s):  
Jaroslav Padevět ◽  
Marcus G Schrems ◽  
Robin Scheil ◽  
Andreas Pfaltz
Keyword(s):  
Asymmetric Catalysis ◽  
Asymmetric Hydrogenation ◽  
Tertiary Alcohol ◽  
Allylic Substitution ◽  
Ligand System ◽  
Methoxycarbonyl Group ◽  
Palladium Catalyzed ◽  
Stereogenic Center

A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central intermediate is a NeoPHOX derivative bearing a methoxycarbonyl group at the stereogenic center next to the oxazoline N atom. The addition of methylmagnesium chloride leads to a tertiary alcohol, which can be acylated or silylated to produce NeoPHOX ligands with different sterical demand. The new NeoPHOX ligands were tested in the iridium-catalyzed asymmetric hydrogenation and palladium-catalyzed allylic substitution. In both reactions high enantioselectivities were achieved, that were comparable to the enantioselectivities obtained with the up to now best NeoPHOX ligand derived from expensive tert-leucine.

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.

Palladium-Catalyzed Asymmetric Allylic Substitution Using Phosphoramidite Ligands Bearing 1,1-Binaphthyl Skeleton

2008 ◽  
Vol 5 (5) ◽  
pp. 346-348 ◽  
Author(s):  
Yongguang Gao ◽  
Xinsheng Li ◽  
Weiyi Chen ◽  
Dongcheng Xu
Keyword(s):  
Allylic Substitution ◽  
Palladium Catalyzed

Origins of Enantioselectivity with Nitrogen−Sulfur Chelate Ligands in Palladium-Catalyzed Allylic Substitution

1999 ◽  
Vol 64 (22) ◽  
pp. 8256-8262 ◽  
Author(s):  
Harry Adams ◽  
James C. Anderson ◽  
Rachel Cubbon ◽  
Daniel S. James ◽  
John P. Mathias
Keyword(s):  
Allylic Substitution ◽  
Chelate Ligands ◽  
Palladium Catalyzed
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