An asymmetric allylic alkylation reaction of 3-alkylidene oxindoles

2015 ◽  
Vol 51 (76) ◽  
pp. 14342-14345 ◽  
Author(s):  
Junjun Feng ◽  
Xin Li ◽  
Jin-Pei Cheng
Keyword(s):  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

An efficient asymmetric allylic alkylation reaction with respect to 3-alkylidene oxindoles and racemic MBH carbonate has been achieved.

Coordination of the Trost modular ligand to palladium allyl fragments: Oligomers, monomers and memory effects in catalysis

2004 ◽  
Vol 76 (3) ◽  
pp. 589-601 ◽  
Author(s):  
G. C. Lloyd-Jones ◽  
S. C. Stephen ◽  
I. J. S. Fairlamb ◽  
Aina Martorell ◽  
Beatriz Dominguez ◽  
...  
Keyword(s):  
Crucial Role ◽  
Dynamic Equilibrium ◽  
Catalyst System ◽  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Monomeric Form ◽  
X Ray Diffraction ◽  
Asymmetric Allylic Alkylation ◽  
X Ray ◽  
Oligomeric Form

Reaction of the C2-symmetric "Trost modular ligand" with cationic Pd(II) allyl fragments allows isolation of air- and bench-stable pro-catalysts for the asymmetric allylic alkylation of racemic cycloalkenyl esters. In solution, three distinct complexation modes are observed. When mixed in a ligand/Pd ratio of 1/2, a binuclear bis-P,O-chelate complex is generated. This species does not induce enantioselectivity in the reaction. In contrast, with a ligand/Pd ratio of 1/1, a highly enantioselective, P,P-coordinated pro-catalyst system is generated in which there are two basic coordination modes: monomeric and oligomeric. The monomeric form is mononuclear and exists as two 13-membered chelates, isomeric through loss of C2-symmetry in the ligand. The oligomeric form is polynuclear and forms chains and rings of alternating ligand and cationic Pd(allyl) units, one of which was identified by single-crystal X-ray diffraction. In solution, the monomeric and oligomeric species are in dynamic equilibrium with populations and interconversion rates controlled by concentration, temperature, and counterion. Isotopic desymmetrization analysis suggests that the monomer-oligomer equilibrium plays a crucial role in both the selectivity and efficiency of the asymmetric allylic alkylation reaction.

scholarly journals Palladium-Catalyzed Asymmetric Allylic Alkylation Reaction of 2-Mono­substituted Indolin-3-ones

Synthesis ◽  
2014 ◽  
Vol 47 (01) ◽  
pp. 134-140 ◽  
Author(s):  
Xue-Long Hou ◽  
Tie-Gen Chen ◽  
Ping Fang ◽  
Li-Xin Dai
Keyword(s):  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation ◽  
Palladium Catalyzed

Highly tunable anionic tethered N-heterocyclic carbene of Pd(II) complexes for asymmetric allylic alkylation reaction

2013 ◽  
Vol 726 ◽  
pp. 46-55 ◽  
Author(s):  
Hiroshi Shirasaki ◽  
Miaki Kawakami ◽  
Haruka Yamada ◽  
Ryuichi Arakawa ◽  
Satoshi Sakaguchi
Keyword(s):  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

scholarly journals Enantioselective synthesis of gem-disubstituted N-Boc diazaheterocycles via decarboxylative asymmetric allylic alkylation

2019 ◽  
Vol 10 (3) ◽  
pp. 788-792 ◽  
Author(s):  
Alexander W. Sun ◽  
Stephan N. Hess ◽  
Brian M. Stoltz
Keyword(s):  
Enantioselective Synthesis ◽  
Alkylation Reaction ◽  
Allylic Alkylation ◽  
Asymmetric Allylic Alkylation

An enantioselective synthesis of diverse N4-Boc-protected α,α-disubstituted piperazin-2-ones and tetrahydropyrimidin-2-ones using the palladiumcatalyzed decarboxylative allylic alkylation reaction has been achieved.

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