Catalytic Asymmetric Roskamp Reaction of α-Alkyl-α-diazoesters with Aromatic Aldehydes: Highly Enantioselective Synthesis of α-Alkyl-β-keto Esters

2010 ◽  
Vol 132 (25) ◽  
pp. 8532-8533 ◽  
Author(s):  
Wei Li ◽  
Jun Wang ◽  
Xiaolei Hu ◽  
Ke Shen ◽  
Wentao Wang ◽  
...  
Keyword(s):  
Aromatic Aldehydes ◽  
Enantioselective Synthesis ◽  
Keto Esters ◽  
Catalytic Asymmetric

Catalytic Asymmetric Domino Michael/Annulation Reaction of Bifunctional Chromone Synthons with β,γ-Unsaturated α-Keto Esters: Rapid Access to Polysubstituted Spirocyclic Hexahydroxanthones

Synthesis ◽  
2020 ◽  
Author(s):  
Xiong-Li Liu ◽  
Ying Zhou ◽  
Hao-Jie Zhou ◽  
Wei Zhou ◽  
You-Ping Tian ◽  
...  
Keyword(s):  
Michael Reaction ◽  
Scale Up ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Biologically Relevant ◽  
Keto Esters ◽  
Rapid Access ◽  
Stereogenic Centers ◽  
Catalytic Asymmetric

A thiourea-catalyzed asymmetric domino Michael/annulation process was devised employing bifunctional oxindole-chromones as C4 synthons and β,γ-unsaturated α-keto esters as C2 synthons. This reaction enables the highly diastereo- and enantioselective synthesis of a range of biologically relevant spirocyclic hexahydroxanthones with one quaternary and four tertiary stereogenic centers, also featuring an intriguing combination of two privileged motifs, including hexahydroxanthone and oxindole substructures, in good yields (up to 76%) and excellent stereoselectivities (up to >99% ee and >20:1 dr). Moreover, using β,γ-unsaturated α-keto esters as the C2 building blocks, which are different from enone substrates such as chalcone and benzalacetone, with the reversible Michael reaction further expanded the scope of the method. In addition, scale-up also demonstrated the applicability of this protocol.

scholarly journals Enantioselective synthesis of (−)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction

2016 ◽  
Vol 14 (1) ◽  
pp. 93-96 ◽  
Author(s):  
Allegra Franchino ◽  
Pavol Jakubec ◽  
Darren J. Dixon
Keyword(s):  
Aldol Reaction ◽  
Enantioselective Synthesis ◽  
Asymmetric Aldol ◽  
Asymmetric Aldol Reaction ◽  
Catalytic Asymmetric

A concise synthesis of (−)-chloramphenicol, based on the catalytic asymmetric aldol reaction between 4-nitrobenzaldehyde and benzhydryl isocyanoacetate, is reported.

Modular Synthesis of Ar-BINMOL-Phos for Catalytic Asymmetric Alkynylation of Aromatic Aldehydes with Unexpected Reversal of Enantioselectivity

2014 ◽  
Vol 356 (8) ◽  
pp. 1708-1718 ◽  
Author(s):  
Tao Song ◽  
Long-Sheng Zheng ◽  
Fei Ye ◽  
Wen-Hui Deng ◽  
Yun-Long Wei ◽  
...  
Keyword(s):  
Aromatic Aldehydes ◽  
Modular Synthesis ◽  
Catalytic Asymmetric

Catalytic Asymmetric Addition of Dimethylzinc to α-Keto Esters

Synfacts ◽  
2006 ◽  
Vol 2006 (6) ◽  
pp. 0593-0593
Author(s):  
J. Pedro ◽  
G. Blay ◽  
I. Fernández ◽  
A. Marco-Aleixandre
Keyword(s):  
Asymmetric Addition ◽  
Keto Esters ◽  
Catalytic Asymmetric
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