Enantioselective synthesis of 8-azabicyclo[3.2.1]octanes via asymmetric 1,3-dipolar cycloadditions of cyclic azomethine ylides using a dual catalytic system

2019 ◽  
Vol 55 (11) ◽  
pp. 1552-1555 ◽  
Author(s):  
Hiroyuki Suga ◽  
Masahiro Yoshiwara ◽  
Takaaki Yamaguchi ◽  
Takashi Bando ◽  
Mizuki Taguchi ◽  
...  
Keyword(s):  
Catalytic System ◽  
Enantioselective Synthesis ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
System P

The asymmetric 1,3-dipolar cycloaddition between diazo imine-derived cyclic azomethine ylides and acryloylpyrazolidinone using a dual catalytic system is reported.

A novel enantioselective synthesis of 6H-dibenzopyran derivatives by combined palladium/norbornene and cinchona alkaloid catalysis

2015 ◽  
Vol 13 (8) ◽  
pp. 2260-2263 ◽  
Author(s):  
Di Xu ◽  
Li Dai ◽  
Marta Catellani ◽  
Elena Motti ◽  
Nicola Della Ca’ ◽  
...  
Keyword(s):  
Catalytic System ◽  
Enantioselective Synthesis ◽  
Cinchona Alkaloid ◽  
System P ◽  
First Time

Chiral dibenzopyran derivatives were obtained by cinchona alkaloid, as organocatalyst, in combination, for the first time, with palladium/norbornene catalytic system.

scholarly journals Multilayer graphene functionalized through thermal 1,3-dipolar cycloadditions with imino esters: a versatile platform for supported ligands in catalysis

2019 ◽  
Vol 55 (52) ◽  
pp. 7462-7465 ◽  
Author(s):  
Marcos Ferrándiz-Saperas ◽  
Alessio Ghisolfi ◽  
Diego Cazorla-Amorós ◽  
Carmen Nájera ◽  
José M. Sansano
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Multilayer Graphene ◽  
Dipolar Cycloadditions ◽  
Chelating Ligand ◽  
Imino Esters

Multilayer graphene (MLG), obtained by mild sonication of graphite, was functionalized via 1,3-dipolar cycloaddition with azomethine ylides and used as a heterogeneous N,O-chelating ligand to coordinate iridium atomic centers.

scholarly journals Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone

2014 ◽  
Vol 10 ◽  
pp. 352-360 ◽  
Author(s):  
Chuqin Peng ◽  
Jiwei Ren ◽  
Jun-An Xiao ◽  
Honggang Zhang ◽  
Hua Yang ◽  
...  
Keyword(s):  
Substituent Effects ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Nitrobenzoic Acid

1,3-Dipolar cycloadditions of isatins, benzylamine and benzylideneacetones were studied to prepare a series of novel spiropyrrolidine-oxindoles – 4′-acetyl-3′,5′-diarylspiro[indoline-3,2′-pyrrolidin]-2-ones and 3′-acetyl-4′,5′-diarylspiro[indoline-3,2′-pyrrolidine]-2-ones in good yields of up to 94% and with good regioselectivities. Regioselectivities are reversible by the addition of water or 4-nitrobenzoic acid, respectively. The substituent effects on the regioselectivity were also investigated.

Diastereoselective 1,3-Dipolar Cycloadditions and Michael Reactions of Azomethine Ylides to (2R)-3-Benzoyl-4-methylidene-2-phenyloxazolidin-5-one and (2S)-3-Benzoyl-2-t-butyl-4-methylideneoxazolidin-5-one

1998 ◽  
Vol 51 (2) ◽  
pp. 137 ◽  
Author(s):  
Stephen G. Pyne ◽  
Javad Safaei-G. ◽  
Karl Schafer ◽  
Abdollah Javidan ◽  
Brian W. Skelton ◽  
...  
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Dipolar Cycloadditions ◽  
Michael Reactions ◽  
Michael Adducts ◽  
Practical Synthesis ◽  
The Michael Addition ◽  
Acid Esters

The 1,3-dipolar cycloaddition reactions of (1) and (11) with the azomethine ylides derived from N-benzylidene α-amino acid esters (2) proceed with good to high exo-diastereoselectivity giving the cycloadducts (4) and (12), respectively. The cycloaddition adducts can be converted to highly functionalised prolines (14), (15) and (17) in high enantiomeric purities. The Michael addition adducts of (1) and (11) with the azomethine ylides derived from the N-(disubstituted methylidene) α-amino acid esters (18), (19) and (33) allow for a practical synthesis of all four stereoisomers of 4-benzamidopyroglutamate. The stereochemistry of these cycloaddition and Michael adducts has been extensively determined by single-crystal X-ray structural analysis [compounds (4b), (5b,d), (12b,d), (13e), (15), (20), (21) and (27)]. Lithium-chelated transition state structures have been proposed to rationalize the stereochemical outcomes of these reactions.

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